RESEARCH
PUBLICATIONS, PATENTS, AND BOOK CHAPTERS
Eric N. Jacobsen
1.
Wenke, G.; Jacobsen, E. N.; Totten, G. E.; Karydas, A. C.; Rhodes, Y. E.
Silyl Ketene Acetal Chemistry: Steric Limitations in Lewis Acid-Promoted
Addition of Ketones, Synth. Commun. 1983, 13, 449.
2.
Jacobsen, E. N.; Bergman, R. G. Synthesis, Crystal and Molecular
Structure, and Reactions of the Bridging Vinylidenedicobalt Complex (µ-CCH2)(CpCoCO)2.
Reaction with Molybdenum Hydrides to Give a Heteronuclear Cluster Complex, Organometallics
1984, 3, 329.
3.
Jacobsen, E. N.; Totten, G. E.; Wenke, G.; Karydas, A. C.; Rhodes, Y. E.
Steric Effects on the Titanium Tetrachloride-Promoted Dimerization of Silyl
Ketene Acetals, Synth. Commun. 1985, 15, 301.
4.
Jacobsen, E. N.; Bergman, R. G. Synthesis and Chemistry of a Bridging
Vinylidenedicobalt Complex. Evidence for a Non-Chain Radical Mechanism in its
Reaction with Metal Hydrides to Give Heteronuclear Clusters, J. Am. Chem.
Soc. 1985, 107, 2023.
5.
Jacobsen, E. N.; Trost, M. K.; Bergman, R. G. Synthesis of
Organometallic Heterodinuclear µ-Oxo Complexes by Extrusion of Alkenes
from Zirconium/Tungsten Oxaalkyl Complexes, J. Am. Chem. Soc. 1986,
108, 8092.
6.
Jacobsen, E. N.; Markó, I. E.; Mungall, W. S.; Schröder, G. W.;
Sharpless, K. B. Asymmetric Dihydroxylation via Ligand-Accelerated
Catalysis, J. Am. Chem. Soc. 1988, 110, 1968.
7.
Jacobsen, E. N.; Goldberg, K. I.; Bergman, R. G. Rapid, Reversible
Intramolecular C-H Oxidative Addition and H-Exchange in a Heterodinuclear
'Early-Late' Transition Metal Complex, J. Am. Chem. Soc. 1988, 110,
3706.
8.
Jacobsen, E. N.; Markó, I. E.; France, M. B.; Svendsen, J. S.;
Sharpless, K. B. Kinetic Role of Alkaloid Ligands in Asymmetric Catalytic
Dihydroxylation, J. Am. Chem. Soc. 1989, 111, 737.
9.
Wai, J. S. M.; Markó, I. E.; Svendsen, J. S.; Finn, M. G.; Jacobsen, E.
N.; Sharpless, K. B. A Mechanistic Insight Leads to a Greatly Improved
Osmium-Catalyzed Asymmetric Dihydroxylation Process, J. Am. Chem. Soc. 1989,
111, 1123.
10. Svendsen,
J. S.; Markó, I. E.; Jacobsen, E. N.; Pulla Rao, Ch.; Bott, S.; Sharpless, K.
B. On the Structure of Osmium Tetroxide-Cinchona Alkaloid Complexes, J.
Org. Chem. 1989, 54, 2263.
11. Zhang,
W.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. Enantioselective
Epoxidation of Unfunctionalized Olefins Catalyzed by (salen)Manganese
Complexes, J. Am. Chem. Soc. 1990, 112, 28012803.
12. Zhang,
W.; Jacobsen, E. N. Preparation of trans-1,2-Diamino-1,2-Dimethylcyclohexane
via Highly Stereoselective Olefin Oxidation by Dinitrogen Tetroxide, Tetrahedron
Lett. 1991, 32, 17111714.
13. Zhang,
W.; Jacobsen, E. N. Asymmetric Epoxidation with Sodium Hypochlorite Catalyzed
by Readily Available Chiral Mn(III) Salen Complexes, J. Org. Chem. 1991,
56, 22962298.
14. Jacobsen,
E. N.; Zhang, W.; Muci, A. R.; Ecker, J. R.; Deng, L. Highly Enantioselective
Epoxidation Catalysts Derived from 1,2-Diaminocyclohexane, J. Am. Chem.
Soc. 1991, 113, 70637064.
15. Fu,
H.; Look, G. C.; Zhang, W.; Jacobsen, E. N.; Wong, C.-H. Mechanistic Study of
a Synthetically Useful Mono-oxygenase Model Using Hypersensitive Probes cis
and trans-2-phenyl-1-Vinylcyclopropane, J. Org. Chem. 1991,
56, 64976500.
16. Jacobsen,
E. N.; Güler, M. L.; Zhang, W. Electronic Tuning of Asymmetric Catalysts, J.
Am. Chem. Soc. 1991, 113, 67036704.
17. Jacobsen,
E. N. Asymmetric Synthesis, in 1992 Yearbook of Science & Technology,
McGraw-Hill, Inc., New York; 1991, p. 34.
18. Lee,
N. H.; Muci, A. R.; Jacobsen, E. N. Enantiomerically Pure Epoxychromans via
Asymmetric Catalysis, Tetrahedron Lett. 1991, 32, 50555058.
19. Lee,
N. H.; Jacobsen, E. N. Enantioselective Epoxidation of Conjugated Dienes and
Enynes. Trans-Epoxides from Cis-Olefins, Tetrahedron Lett. 1991,
32, 65336536.
20. Deng,
L.; Jacobsen, E. N. A Practical, Highly Enantioselective Synthesis of the
Taxol Side Chain via Asymmetric Catalysis, J. Org. Chem. 1992, 57,
43204323.
21. Pospisil,
P. J.; Jacobsen, E. N. A Substoichiometric PyridineLithium Enolate Complex:
Solution and X-Ray Data, and Implications to Catalysis in the Aldol Reaction, J.
Am. Chem. Soc. 1992, 114, 75857587.
22. Palucki,
M.; Hanson, P.; Jacobsen, E. N. Asymmetric Oxidation of Sulfides with H2O2
Catalyzed by (salen)Mn(III) Complexes, Tetrahedron Lett. 1992, 33,
71117114.
23. Baudry,
M.; Etienne, S.; Bruce, A.; Palucki, M.; Jacobsen, E.; Malfroy, B.
Salen-Manganese Complexes are Superoxide Dismutate Mimics, Biochem.
Biophys. Res. Commun. 1993, 192, 964968.
24. Li, Z.; Conser, K. R.; Jacobsen, E. N. Asymmetric Alkene
Aziridination with Readily Available Chiral Diimine-Based Catalysts, J. Am.
Chem. Soc. 1993, 115, 53265327.
25. Allain,
E. A.; Hager, L. P.; Deng, L.; Jacobsen, E. N. Highly Enantioselective
Epoxidation of Disubstituted Alkenes with Hydrogen Peroxide Catalyzed by
Chloroperoxidase, J. Am. Chem. Soc. 1993, 115, 44154416.
26. Heinze,
K. F.; Allen, J. L.; Jacobsen, E. N. Encouraging Tomorrow's Chemists:
University Outreach Program Bringing Hands-On Experiments to Local Students, J.
Chem. Educ. 1995, 72, 167169.
27. Jacobsen,
E. N. Asymmetric Catalytic Epoxidation of Unfunctionalized Olefins, in Catalytic
Asymmetric Synthesis, Ojima, I., Ed.; VCH: New York, 1993; Chapter 4.2.
28. Fields,
L. B.; Jacobsen, E. N. Synthesis and Characterization of Chiral Bimetallic
Complexes Bearing Hard and Soft Lewis Acidic Sites, Tetrahedron: Asymmetry
1993, 4, 22292240.
29. Chang,
S.; Lee, N. H.; Jacobsen, E. N. Regio- and Enantioselective Epoxidation of
Conjugated Polyenes. Formal Synthesis of LTA4 Methyl Ester, J.
Org. Chem. 1993, 58, 69396941.
30. Zhang,
W.; Lee, N. H.; Jacobsen, E. N. Non-Stereospecific Mechanisms in Asymmetric
Addition to Alkenes Result in Enantiodifferentiation after the First
Irreversible Step, J. Am. Chem. Soc. 1994, 116, 425426.
31. Jacobsen,
E. N.; Deng, L.; Furukawa, Y.; Martínez, L. E. Enantioselective Catalytic
Epoxidation of Cinnamate Esters, Tetrahedron 1994, 50,
43234334.
32. Chang,
S.; Heid, R. M.; Jacobsen, E. N. Enantioselective Epoxidation of Cyclic
1,3-Dienes Catalyzed by a Sterically and Electronically Optimized (Salen)Mn
Complex, Tetrahedron Lett. 1994, 35, 669672.
33. Larrow,
J. F.; Jacobsen, E. N.; Gao, Y.; Hong, Y.; Nie, X.; Zepp, C. M. A Practical
Process for the Large-Scale Preparation of (R,R)-N,N-Bis(3,5-Di-tert-butylsalicylidene)-1,2-Cyclohexanediaminomanganese
(III) Chloride, a Highly Enantioselective Epoxidation Catalyst, J. Org.
Chem. 1994, 59, 19391940.
34. Chang,
S.; Galvin, J. M.; Jacobsen, E. N. Effect of Chiral Quaternary Ammonium Salts
on (salen)Mn-Catalyzed Epoxidation of cis-Olefins. A Highly Enantioselective,
Catalytic Route to Trans Epoxides, J. Am. Chem. Soc. 1994, 116,
69376938.
35. Brandes,
B. D.; Jacobsen, E. N. Highly Enantioselective, Catalytic Epoxidation of
Trisubstituted Olefins, J. Org. Chem. 1994, 59, 43784380.
36. Palucki,
M.; Pospisil, P. J.; Zhang, W.; Jacobsen, E. N. Highly Enantioselective, Low
Temperature Epoxidation of Terminal Olefins, J. Am. Chem. Soc. 1994,
116, 93339334.
37. Larrow,
J. F.; Jacobsen, E. N. Kinetic Resolution of 1,2-Dihydronaphthalene Oxide and
Related Epoxides via Asymmetric CH Hydroxylation, J. Am. Chem. Soc. 1994,
116, 1212912130.
38. Jacobsen,
E. N.; Finney, N. S. Synthetic and Biological Catalysts for Chemical
Synthesis: How to Assess Practical Utility, Chem. Biol. 1994, 1,
8590.
39. Hansen,
K. H.; Finney, N. S.; Jacobsen, E. N. Carbenoid Transfer to Imines: A New
Asymmetric Catalytic Synthesis of Aziridines, Angew. Chem. Int. Ed. Engl.
1995, 34, 676678.
40. Jacobsen,
E. N.; Galvin, J. M. Sodium Hypochlorite, in Encyclopedia of Reagents for
Organic Synthesis, Volume 7, Paquette, L.A., Ed.; Wiley: New York, 1995,
pp. 45804585.
41. Jacobsen,
E. N. Sodium Hypochlorite-Chiral Manganese (III) Salen Complexes, in Encyclopedia
of Reagents for Organic Synthesis, Volume 7, Paquette, L.A., Ed.; Wiley:
New York, 1995, pp. 45854586.
42. Martínez,
L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. Highly
Enantioselective Ring Opening of Epoxides Catalyzed by Chiral (salen)Cr(III)
Complexes, J. Am. Chem. Soc. 1995, 117, 58975898.
43. Li,
Z.; Quan, R. W.; Jacobsen, E. N. Mechanistic Study of the (diimine)Cu-Catalyzed
Asymmetric Azridination of Alkenes. Nitrene Transfer via Ligand-Accelerated
Catalysis, J. Am. Chem. Soc. 1995, 117, 58895890.
44. Jacobsen,
E. N. Transition Metal Catalyzed Oxidations: Asymmetric Epoxidation , in Comprehensive
Organometallic Chemistry II, Vol. 12, Wilkinson, G.; Stone, F. G. A.; Abel,
E. W.; Hegedus, L. S., Eds.; Pergamon: New York; 1995, pp. 10971135.
45. Jacobsen,
E. N. Fundamental and Applied Studies in Asymmetric Oxidation Catalysis, in Stereoselective
Reactions of Metal-Activated Molecules, Werner, H. and Sundmeyer, J., Eds.;
Vieweg: New York; 1995, pp. 1726.
46. Brandes,
B. D.; Jacobsen, E. N. Enantioselective Catalytic Epoxidation of
Tetrasubstituted Olefins, Tetrahedron Lett. 1995, 36, 51235126.
47. Palucki,
M.; McCormick, G. J.; Jacobsen, E. N. Low Temperature Asymmetric Epoxidation
of Unfunctionalized Olefins Catalyzed by (salen)Mn(III) Complexes, Tetrahedron
Lett. 1995, 36, 54575460.
48. Vander
Velde, S. L.; Jacobsen, E. N. Kinetic Resolution of Racemic Chromenes via
Asymmetric Epoxidation; Synthesis of (+)-Teretifolione B, J. Org. Chem.
1995, 60, 53805381.
49. Leighton,
J.L.; Jacobsen, E.N. Efficient Synthesis of (R)-4-Trimethylsilyloxy-2-
cyclopentenone by Enantioselective Catalytic Epoxide Ring Opening, J. Org.Chem.
1996, 61, 389390.
50. Larrow,
J.F.; Schaus, S.E.; Jacobsen, E.N. Kinetic Resolution of Terminal Epoxides via
Highly Regioselective and Enantioselective Ring Opening with TMSN3.
An Efficient, Catalytic Route to 1,2-Aminoalcohols, J. Am. Chem. Soc. 1996,
118, 74207421.
51. Pospisil,
P.J.; Carsten, D.H.; Jacobsen, E.N. X-Ray Structural Studies of Highly
Enantioselective Mn(salen) Epoxidation Catalysts, Chem. Eur. J. 1996,
2, 974980.
52. Quan,
R.W.; Li, Z.; Jacobsen, E.N. Enantioselective Binding of Prochiral Olefins to
a Chiral Catalyst via Simultaneous Face-Face and Edge-Face Aromatic
Interactions, J. Am. Chem. Soc. 1996, 118, 81568157.
53. Francis,
M.B.; Finney, N.S.; Jacobsen, E.N. Combinatorial Approach to the Discovery of
Novel Coordination Compounds," J. Am. Chem. Soc. 1996, 118,
89838984.
54. Martinez, L.E.; Nugent, W.A.; Jacobsen, E.N. Highly Efficient and Enantioselective
Synthesis of Carbocyclic Nucleoside Analogs Using Selective Early Transition
Metal Catalysis, J. Org. Chem. 1996, 61, 79637966.
55. Schaus,
S.E.; Jacobsen, E.N. Dynamic Kinetic Resolution of Epichlorohydrin via
Enantioselective Catalytic Ring Opening with TMSN3. Practical
Synthesis of Aryl Oxazolidinone Antibacterial Agents, Tetrahedron Lett.
1996, 37, 79397942.
56. Hansen,
K.B.; Leighton, J.L.; Jacobsen, E.N. On the Mechanism of Asymmetric
Nucleophilic Ring-Opening of Epoxides Catalyzed by (Salen)Cr(III) Complexes, J.
Am. Chem. Soc. 1996, 118, 1092410925.
57. Jacobsen,
E.N.; Kakiuchi, F.; Konsler, R.G.; Larrow, J.F.; Tokunaga, M. Enantioselective
Catalytic Ring Opening of Epoxides with Carboxylic Acids, Tetrahedron Lett.
1997, 38, 773776.
58. Wu,
M.H.; Jacobsen, E.N. An Efficient Formal Synthesis of Balanol via the
Asymmetric Epoxide Ring Opening Reaction, Tetrahedron Lett. 1997,
38, 16931696.
59. Schaus,
S.E.; Larrow, J.F.; Jacobsen, E.N. Practical Synthesis of Enantiopure Cyclic
1,2-Aminoalcohols via Catalytic Asymmetric Ring Opening of Meso Epoxides, J.
Org. Chem. 1997, 62, 41974199.
60. Jacobsen,
E.N.; Zhang, W.; Deng, L. Chiral Catalysts and Epoxidation Reactions Catalyzed
Thereby, U.S. Patent No. 5, 637, 739 issued 6/10/97.
61. Jacobsen,
E.N.; Zhang, W.; Deng, L. Chiral Catalysts and Epoxidation Reactions, U.S.
Patent No. 5, 663, 393 issued 9/2/97.
62. Tokunaga,
M.; Larrow, J.F.; Kakiuchi, F.; Jacobsen, E.N. Asymmetric Catalysis with
Water: Efficient Kinetic Resolution of Terminal Epoxides by Means of Catalytic
Hydrolysis, Science 1997, 277, 936938.
63. Finney, N.S.; Pospisil, P.J.; Chang, S.; Palucki, M.; Hansen, K.B.; Jacobsen, E.N. On the
Viability of Metallaoxetane Intermediates in the (salen)Mn-Catalyzed Asymmetric
Epoxidation Reaction, Angew. Chem. Int. Ed. Engl. 1997, 36,
17201723.
64. Jacobsen,
E.N.; Martinez, L.E.; Leighton, J.L. Stereoselective Ring Opening Reactions,
U.S. Patent No. 5, 665, 890 issued 9/9/97.
65. Brandes,
B.D.; Jacobsen, E.N. Synthesis of Enantiopure 3-Chlorostyrene Oxide via an
Asymmetric Epoxidation/Hydrolytic Kinetic Resolution Sequence, Tetrahedron:
Asymmetry 1997, 8, 39273933.
66. Larrow,
J.F.; Jacobsen, E.N. (R,R)-N,N'-Bis(3,5-Di-tert-butylsalicylidene)-1,2-
Cyclohexanediaminomanganese (III) Chloride, a Highly Enantioselective
Epoxidation Catalyst, Organic Synth. 1997, 75, 110.
67. Schaus,
S.E.; Brånalt, J.E.; Jacobsen, E.N. Asymmetric Hetero-Diels-Alder Reactions
Catalyzed by Chiral (salen)Chromium(III) Complexes, J. Org. Chem. 1998,
63, 403405.
68. Palucki,
M.; Finney, N.S.; Pospisil, P.J.; Güler, M.L.; Ishida, T.; Jacobsen, E.N. The
Mechanistic Basis for Electronic Effects on Enantioselectivity in the
(salen)Mn-Catalyzed Epoxidation Reaction, J. Am. Chem. Soc. 1998,
120, 948954.
69. Sigman,
M.S.; Jacobsen, E.N. Schiff Base Catalysts for the Asymmetric Strecker
Reaction Identified and Optimized from Parallel Synthetic Libraries, J. Am.
Chem. Soc. 1998, 120, 49014902.
70. Sigman,
M.S.; Jacobsen, E.N. Enantioselective Addition of Hydrogen Cyanide to Imines
Catalyzed by a Chiral (salen)Al(III) Complex, J. Am. Chem. Soc. 1998,
120, 53155316.
71. Francis,
M.B.; Jamison, T.F.; Jacobsen, E.N. Combinatorial Libraries of Transition
Metal Complexes, Catalysts, and Materials, Curr. Opinion Chem. Biol. 1998,
2, 422428.
72. Schaus,
S.E.; Brånalt, J.E.; Jacobsen, E.N. Total Synthesis of Muconin by Efficient
Assembly of Chiral Building Blocks, J. Org. Chem. 1998, 63,
48764877.
73. Wu,
M.H.; Jacobsen, E.N. Asymmetric Ring Opening of Meso Epoxides with Thiols:
Enantiomeric Enrichment Using a Bifunctional Nucleophile, J. Org. Chem.
1998, 63, 52525254.
74. Annis,
D.A.; Jacobsen, E.N. Solid Phase Synthesis of Cyclic RGD Peptide Derivatives
via Asymmetric Catalysis: Stereochemistry as a Diversity Element, Angew.
Chem. Int. Ed. 1998, 37, 19071909.
75. Furrow,
M.E.; Schaus, S.E.; Jacobsen, E.N. Practical Access to Highly
Enantioenriched C-3 Building Blocks via Hydrolytic Kinetic Resolution, J.
Org. Chem. 1998, 63, 67766777.
76. Konsler,
R.G.; Karl, J.; Jacobsen, E.N. Cooperative Asymmetric Catalysis Using Dimeric
Salen Complexes, J. Am. Chem. Soc. 1998, 120, 1078010781.
77. Dakin,
L. A.; Schaus, S.E.; Jacobsen, E.N.; Panek, J.S., Carbenoid Insertions into
the Silicon-Hydrogen Bond Catalyzed by Chiral Copper (I) Schiff Base
Complexes, Tetrahedron Lett. 1998, 39, 89478950.
78. Lebel,
H.; Jacobsen, E.N. Enantioselective Total Synthesis of Taurospongin A, J.
Org. Chem. 1998, 63, 96249625.
79. Larrow,
J.F.; Roberts, E.; Verhoeven, T.R.; Ryan, K.M.; Senanayake, C.H.; Reider, P.J.;
Jacobsen, E.N. (1S,2R)-1-Aminoindan-2-ol, Organic Synth.
1998, 76, 4656.
80. Hinterding,
K.; Jacobsen, E.N. Regioselective Carbomethoxylation of Chiral Epoxides: a New
Route to Enantiomerically Pure b-Hydroxyesters,
J. Org. Chem. 1999, 64, 21642165.
81. Francis,
M. B.; Jacobsen, E. N. Discovery of Novel Catalysts for Alkene Epoxidation
Using Metal-Binding Combinatorial Libraries, Angew. Chem. Int. Ed. 1999,
38, 937941.
82. Annis,
D. A.; Jacobsen, E. N. Polymer-Supported Chiral Co(Salen) Complexes: Synthetic
Applications and Mechanistic Investigations in the Hydrolytic Kinetic
Resolution of Terminal Epoxides, J. Am. Chem. Soc. 1999, 121,
41474154.
83. Senanayake,
C. H.; Jacobsen, E. N. Chiral (Salen)Mn(III) Complexes in Asymmetric
Epoxidations: Practical Synthesis of cis-Aminoindanol and Its
Application to Enantiopure Drug Synthesis, in Process Chemistry in the
Pharmaceutical Industry, Gadamasetti, K. G., Ed.; Dekker: New York, 1999,
pp. 347368.
84. Ready,
J. M.; Jacobsen, E. N. Asymmetric Catalytic Synthesis of a-Aryloxy Alcohols: Kinetic Resolution of
Terminal Epoxides via Highly Enantioselective Ring Opening with Phenols, J.
Am. Chem. Soc. 1999, 121, 60866087.
85. Wu,
M. H.; Hansen, K. B.; Jacobsen, E. N. Regio- and Enantioselective Cyclization
of Epoxy Alcohols Catalyzed by a [CoIII(salen)] Complex, Angew.
Chem. Int. Ed. 1999, 38, 20122014.
86. Jacobsen,
E. N.; Martinez, L. E.; Leighton, J. L. Stereoselective Ring Opening
Reactions, U.S. Patent No. 5, 929, 232 issued 7/27/99.
87. Dossetter,
A. G.; Jamison, T. F.; Jacobsen, E. N. Highly Enantio- and Diastereoselective
Hetero-Diels-Alder Reactions Catalyzed by New Chiral Tridentate Chromium
Catalysts, Angew. Chem. Int. Ed. 1999, 38,
23982400.
88. Lebel,
H.; Jacobsen, E. N. Chromium Catalyzed Kinetic Resolution of 2,2-Disubstituted
Epoxides, Tetrahedron Lett. 1999, 40, 73037306.
89. Myers,
J. K.; Jacobsen, E. N. Asymmetric Synthesis of b-Amino
Acid Derivatives via Catalytic Conjugate Addition of Hydrazoic Acid to
Unsaturated Imides, J. Am. Chem. Soc. 1999, 121, 89598960.
90. Jacobsen,
E. N.; Wu, M. H. Epoxidation of Alkenes Other than Allylic Alcohols, in Comprehensive
Asymmetric Catalysis, Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.;
Springer: New York; 1999, Chapter 18.2.
91. Jacobsen,
E. N.; Wu, M. H. Ring Opening of Epoxides and Related Reactions, in Comprehensive
Asymmetric Catalysis, Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.;
Springer: New York; 1999, Chapter 35.
92. Jacobsen,
E. N. Aziridination, in Comprehensive Asymmetric Catalysis, Jacobsen,
E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: New York; 1999, Chapter 17.
93. Jacobsen,
E. N. Future Perspectives in Asymmetric Catalysis, in Comprehensive Asymmetric
Catalysis, Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: New
York; 1999, Chapter 42.
94. Peukert,
S.; Jacobsen, E. N. Enantioselective Parallel Synthesis Using
Polymer-Supported Chiral Co(Salen) Complexes, Org. Lett. 1999, 1,
12451248.
95. Li,
Z.; Fernandez, M.; Jacobsen, E. N. Enantioselective Ring-opening of meso
Aziridines Catalyzed by Tridentate Schiff-base Chromium(III) Complexes, Org.
Lett. 1999, 1, 16111613.
96. Jacobsen,
E. N.; Breinbauer, R. Nickel Comes Full Cycle, (Perspective) Science 2000,
287, 437.
97. Sigman,
M. S.; Vachal, P.; Jacobsen, E. N. A General Catalyst for the Asymmetric
Strecker Reaction, Angew. Chem. Int. Ed. 2000, 39, 12791281.
98. Vachal,
P.; Jacobsen, E. N. Enantioselective Catalytic Addition of HCN to Ketoimines.
Catalytic Synthesis of Quaternary Amino Acids Org. Lett. 2000, 2,
867870.
99. Schaus,
S. E.; Jacobsen, E. N. Asymmetric Ring-Opening of Meso-Epoxides with TMSCN
Catalyzed by (pybox)Lanthanide Complexes, Org. Lett. 2000, 2,
10011004.
100. Jacobsen, E. N. Asymmetric
Catalysis of Epoxide Ring-Opening Reactions, Acc. Chem. Res. 2000,
33, 421431.
101.
Breinbauer, R.; Jacobsen, E. N. Cooperative Asymmetric Catalysis with
Dendrimeric Co(salen) Complexes, Angew. Chem. Int. Ed. 2000, 39,
36043607.
102. Jacobsen, E. N.; Schaus, S.
E. "Asymmetric Cycloaddition Reactions," U.S. Patent No. 6,130,340
issued 10/10/00.
103. Thompson, C. F.; Jamison, T.
F.; Jacobsen, E. N. Total Synthesis of FR901464. Convergent Assembly of
Chiral Components Prepared by Asymmetric Catalysis, J. Am. Chem. Soc. 2000,
122, 1048210483.
104. Keith, J. M.; Larrow, J. F.;
Jacobsen, E. N. Practical Considerations in Kinetic Resolution Reactions, Adv.
Synth. & Catal. 2001, 343, 526.
105.
Su, J. T.; Vachal, P.; Jacobsen, E. N. Practical Synthesis of a Soluble
Schiff Base Catalyst for the Asymmetric Strecker Reaction, Adv. Synth.
& Catal. 2001, 343, 197200.
106.
Ready, J. M.; Jacobsen, E. N. Highly Active Oligomeric (salen)Co Catalysts
for Asymmetric Epoxide Ring Opening Reactions, J. Am. Chem. Soc. 2001,
123, 26872688.
107.
Jacobsen, E. N.; Schaus, S. E.; Dossetter, A. G.; Jamison, T. F.
Asymmetric Cycloaddition Reactions, U.S. Patent #6,211,370 issued 4/3/01.
108.
Brandes, B. D.; Jacobsen, E. N. Regioselective Ring Opening of
Enantiomerically Enriched Epoxides via Catalysis with Chiral (Salen)Cr(III)
Complexes, Synlett 2001, 10131015.
109.
White, M. C.; Doyle, A. G.; Jacobsen, E. N. Synthetically Useful,
Self-Assembling MMO Mimic System for Catalytic Alkene Epoxidation with Aqueous
H2O2, J. Am. Chem. Soc. 2001, 123, 71947195.
110.
Jacobsen, E. N.; Tokunaga, M.; Larrow, J. F. Hydrolytic Kinetic
Resolution of Cyclic Substrates U.S. Patent No. 6,262,278 B1 issued 7/17/01.
111.
Chavez,
D. E.; Jacobsen, E. N. Total Synthesis of Fostriecin (CI-920), Angew.
Chem. Int. Ed. 2001, 40, 36673670.
112.
Thompson, C. F.; Jamison, T. F.; Jacobsen, E. N. FR901464: Total
Synthesis, Proof of Structure, and Evaluation of Synthetic Analogs, J. Am. Chem. Soc. 2001, 123,
99749983.
113.
Liu,
P.; Jacobsen, E. N. Total Synthesis of (+)-Ambruticin, J. Am. Chem. Soc.
2001, 123, 1077210773.
114.
Jacobsen, E. N., Sigman, M. S. Parallel Combinatorial Approach to the
Discovery and Optimization of Catalysts and Uses Thereof, U.S. Patent
#6,316,616, issued 11/13/01
115.
Schaus, S. E.; Brandes, B. D; Larrow, J. F.; Tokunaga, M.; Hansen, K.
B.; Gould, A. E.; Furrow, M. E.; Jacobsen, E. N. Highly Selective
Hydrolytic Kinetic Resolution of Terminal Epoxides Catalyzed by Chiral
(salen)Cobalt(III)-Complexes. Practical Synthesis of Enantioenriched Terminal
Epoxides and 1,2-Diols, J. Am. Chem. Soc. 2002, 124, 13071315.
116.
Movassaghi, M.; Jacobsen, E. N. A Direct Method for the Conversion of
Terminal Epoxides into g-Butanolides, J. Am. Chem. Soc. 2002, 124, 24562457.
117.
Ruck,
R. T.; Jacobsen, E. N. Asymmetric Catalysis of Hetero-Ene Reactions with
Tridentate Schiff Base Chromium(III) Complexes, J. Am. Chem. Soc. 2002,
124, 28822883.
118.
Ready,
J. R.; Jacobsen, E. N. A Practical Oligomeric (salen)Co Catalyst for
Asymmetric Epoxide Ring Opening Reactions, Angew. Chem. Int. Ed. 2002,
41, 13741377.
119.
Joly, G. D.; Jacobsen,
E. N. Catalyst-Controlled Diastereoselective Hetero-DielsAlder
Reactions, Organic Lett. 2002, 4, 17951798.
120.
Jacobsen, E. N.; Schaus, S. E.; Dossetter, A. G.; Jamison, T. F.
Asymmetric Cycloaddition Reactions, U.S. Patent #6,369,223 issued 4/9/02.
121.
Gademann, K.; Chavez, D. E.; Jacobsen, E. N. Highly Enantioselctive
Inverse Electron Demand Hetero-DielsAlder Reactions of a,b-Unsaturated
Aldehydes, Angew. Chem. Int. Ed. 2002, 41, 30593061.
122.
Jacobsen, E. N.; Francis, M. B.; Finney, N. S. "Combinatorial
Approach for Generating Novel Coordination Complexes," U.S. Patent
#6,489,093 issued 12/3/02.
123.
Vachal, P.; Jacobsen, E. N. Structure-Based Analysis and Optimization
of a Highly Enantioselective Catalyst for the Strecker Reaction, J. Am. Chem. Soc. 2002, 124, 1001210014.
124.
Jacobsen, E. N.; Tokunaga, M.; Larrow, J. F. Hydrolytic Kinetic
Resolution of Cyclic Substrates U.S. Patent # 6,448,414 issued 9/10/02.
125.
Goodman,
S. N.; Jacobsen, E. N. A Practical Synthesis of a,b-Unsaturated Imides, Useful Substrates For Asymmetric
Conjugate Addition Reactions, Adv. Synth. Catal. 2002, 344,
953956.
126.
Wenzel, A. G.; Jacobsen, E. N. Asymmetric Catalytic Mannich Reactions
Catalyzed by Urea Derivatives: Enantioselective Synthesis of b-Aryl-b-Amino
Acids, J. Am. Chem. Soc. 2002, 124, 1296412965.
127.
Movassaghi, M.;
Jacobsen, E. N. The Simplest Enzyme, (Perspective) Science 2002,
298, 19041905.
128.
Goodman,
S. N.; Jacobsen, E. N. Enantiopure b-Hydroxy
Morpholine Amides From Terminal Epoxides via Carbonylation at 1 Atm, Angew.
Chem. Int. Ed. 2002, 41, 47034705.
129.
Yoon, T. P.; Jacobsen, E. N. Privileged Chiral Catalysts, Science
2003, 299, 16911693.
130.
Sammis, G. M.; Jacobsen, E. N. Highly Enantioselective, Catalytic
Conjugate Addition of Cyanide to a,b-Unsaturated Imides, J. Am. Chem. Soc. 2003, 125, 44424443.
131.
Jacobsen, E. N., Sigman, M. S. "Main Group Metal-Based Asymmetric
Catalysts and Applications Thereof," U.S. Patent #6,521,561 issued
2/18/03.
132.
Chavez, D. E.; Jacobsen,
E. N. Catalyst-Controlled Inverse Electron Demand Hetero-DielsAlder
Reactions in the Enantio- and Diastereoselective Synthesis of Iridoid Natural
Products, Org. Lett. 2003, 5, 25632565.
133. Taylor, M. S.;
Jacobsen, E. N. Enantioselective Michael Additions to a,b-Unsaturated
Imides Catalyzed by a Salen-Al Complex, J. Am. Chem. Soc. 2003, 125, 1120411205.
134.
Wenzel, A. G.; Lalonde, M. P.; Jacobsen, E. N. Divergent
Stereoinduction Mechanisms in Urea-Catalyzed Additions to Imines, Synlett
2003, 12, 19191922.
135.
Ruck, R. T.; Jacobsen, E. N. Asymmetric Hetero-Ene Reactions of
Trimethylsilyl Enol Ethers Catalyzed by Tridentate Schiff Base Chromium(III)
Complexes, Angew. Chem. Int. Ed. 2003, 42, 47714774.
136. White, D. E.; Jacobsen, E.
N. New Oligomeric Catalyst for the Hydrolytic Kinetic Resolution of Terminal
Epoxides Under Solvent-Free Conditions, Tetrahedron: Asymm. 2003,
14, 36333638.
137.
Vachal, P.; Jacobsen, E.
N. Cyanation of Carbonyl and Imino
Groups, in Comprehensive Asymmetric Catalysis (1st
Supplement), Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: New York; 2003; Ch. 28.
138.
Keith, J. M.; Jacobsen, E. N. Asymmetric Hydrocyanation of Hydrazones
Catalyzed by Lanthanide PYBOX Complexes Organic Lett. 2004,
6, 153155.
139.
Raheem, I. T.; Goodman, S. N.; Jacobsen, E. N. Catalytic Asymmetric
Total Syntheses of Quinine and Quinidine, J. Am. Chem. Soc. 2004, 126, 706707.
140.
Nielsen, L. C. P.; Stevenson, C. P.; Blackmond, D.G.; Jacobsen, E. N.
Mechanistic Investigation Leads to a Synthetic Improvement in the Hydrolytic
Kinetic Resolution of Terminal Epoxides, J. Am. Chem. Soc. 2004, 126, 13601362.
141.
Liu, Y.; DiMare, M.; Marchese, S. A.; Jacobsen, E. N.; Jasmin, S.
Hydrolytic Kinetic Resolution of Epoxides, U.S. Patent #6,693,206 issued
2/17/04.
142.
Joly, G. D.; Jacobsen, E. N. Thiourea-Catalyzed Enantioselective
Hydrophosphonylation of Imines: Practical Access to Enantiomerically Enriched a-Amino Phosphonic Acids, J. Am. Chem.
Soc. 2004, 126, 41024103.
143.
Taylor, M. S.; Jacobsen,
E. N. Asymmetric Catalysis in Complex Target Synthesis, Proc. Nat.
Acad. Sci. 2004, 101, 53685373.
144. Jacobsen,
E. N., Sigman, M. S. "Parallel Combinatorial Approach to the Discovery and
Optimization of Catalysts and Uses Thereof," U.S. Patent #6,709,824 B2
issued 3/23/04.
145. Larrow,
J. F.; Jacobsen, E. N. Asymmetric Processes Catalyzed by Chiral (Salen)Metal
Complexes, Topics Organomet. Chem. 2004, 6, 123152.
146.
Kim, S.; Jacobsen, E. N. General Catalytic Synthesis of Highly
Enantiomerically Enriched Terminal Aziridines from Racemic Epoxides, Angew. Chem. Int. Ed. 2004,
43, 39523954.
147.
Sammis, G. M.; Danjo,
H.; Jacobsen, E. N. Cooperative Dual Catalysis: Application to the
Highly Enantioselective Conjugate Cyanation of Unsaturated Imides, J. Am. Chem. Soc. 2004, 126, 99289929.
148.
Taylor, M. S.; Jacobsen,
E. N. Highly Enantioselective Catalytic Acyl-PictetSpengler Reactions,
J. Am. Chem. Soc. 2004, 126, 1055810559.
149.
Vanderwal, C. D.;
Jacobsen, E. N. Highly Enantioselective Hydration of a,b-Unsaturated
Imides by Al-Catalyzed Conjugate Addition of Oxime Nucleophiles, J. Am.
Chem. Soc. 2004, 126, 1472414725.
150.
Jacobsen, E. N.; Tokunaga, M.; Larrow, J. F. Hydrolytic Kinetic
Resolution of Cyclic Substrates, U.S. Patent #6,800,766 issued 10/5/04.
151.
Doyle, A. G.; Jacobsen, E. N. Enantioselective Alkylations of
Tributyltin Enolates Catalyzed by Cr(salen)Cl: Access to Enantiomerically
Enriched All Carbon Quaternary Centers, J. Am. Chem. Soc. 2005, 127,
6263.
152.
Yoon, T. P.; Jacobsen, E. N. Highly Enantioselective Thiourea-catalyzed
Nitro-Mannich Reaction, Angew. Chem. Int. Ed. 2005, 44,
466468.
153.
Jacobsen, E. N., Sigman, M. S. "Main Group Metal-Based Asymmetric
Catalysts and Applications Thereof," U.S. Patent #6,844,448 issued
1/18/05.
154.
Taylor, M. S.; Zalatan, D. N.; Lerchner, A. M.; Jacobsen, E. N. Highly
Enantioselective Conjugate Additions to a,b-Unsaturated Ketones Catalyzed by a
(salen)Al Complex, J. Am. Chem. Soc. 2005, 127, 13131317.
155.
Gandelman, M.; Jacobsen, E. N. Highly Enantioselective Catalytic Conjugate Addition of
N-Heterocycles to a,b-Unsaturated Ketones and Imides, Angew.
Chem. Int. Ed. 2005, 44, 23932397.
156.
Wenzel, A. G.; Jacobsen,
E. N. Asymmetric Catalysis in the Enantioselective Synthesis of b-Amino Acids, in Enantioselective Synthesis
of beta-Amino Acids, Juaristi, E.; Soloshonok, V., Eds.; Wiley-VCH: New
York, 2005; Chapter 4.
157.
Fuerst, D. E.; Jacobsen, E. N. Thiourea-Catalyzed Enantioselective
Cyanosilylation of Ketones, J. Am. Chem. Soc. 2005, 127,
89648965.
158.
Jarvo, E. R.; Lawrence, B. M.; Jacobsen, E. N. Highly Enantio- and
Regioselective Quinone DielsAlder Reactions Catalyzed by a Tridentate (Schiff
Base)Cr(III) Complex, Angew. Chem. Int. Ed. 2005, 44,
60436046.
159.
Boezio, A. A.; Jarvo, E. R.; Lawrence, B. M.; Jacobsen, E. N. Efficient Total Syntheses of ()-Colombiasin
A and ()-Elisapterosin B: Application of the
Cr-Catalyzed Asymmetric Quinone DielsAlder Reaction, Angew. Chem.
Int. Ed. 2005, 44, 60466050.
160.
Taylor, M. S.; Jacobsen, E. N. Enantioselective
Thiourea-Catalyzed Acyl-Mannich Reactions of Isoquinolines, Angew. Chem.
Int. Ed. 2005, 44, 67006704.
161.
Raheem, I. T.; Jacobsen, E. N. Highly Enantioselective Aza-BaylisHillman
Reactions Catalyzed by Chiral Thiourea Derivatives, Adv. Synth. Catal. 2005,
347, 17011708.
162.
Chavez, D. E.; Jacobsen,
E. N. An Efficient, Highly Diastereo- and Enantioselective Hetero-DielsAlder
Catalyst. Preparation of (2S,6R)-6-(tert-Butyldimethylsilyloxymethyl)-2-Methoxy-2,5-Dihydropyran,
Organic Synth. 2005, 82, 3442.
163.
Nielsen, L. P. C.
Jacobsen, E. N.Catalytic, Asymmetric Epoxide Ring-Opening Chemistry, in Aziridines
and Epoxides in Organic Synthesis, Yudin, A., Ed.; Wiley, New York; 2006, Ch. 10.
164.
Taylor, M. S.; Jacobsen,
E. N. Asymmetric Catalysis by Chiral Hydrogen Bond Donors, Angew.
Chem. Int. Ed. 2006, 45, 15201543.
165.
Balskus, E. P.; Jacobsen, E. N. a,b-Unsaturated
b-Silyl Imide Substrates for Catalytic,
Enantioselective Conjugate Additions: A Total Synthesis of (+)-Lactacystin and
the Discovery of a New Proteasome Inhibitor, J. Am. Chem. Soc. 2006,
128, 68106812.
166.
Huang, H.; Jacobsen, E. N. Highly Enantioselective Direct Conjugate
Addition of Ketones to Nitroalkenes Promoted by A Chiral Primary Amine-Thiourea
Catalyst, J. Am. Chem. Soc. 2006, 128, 71707171.
167.
Lalonde, M. P.; Chen, Y.; Jacobsen, E. N. A Chiral Primary
Amine-Thiourea Catalyst for the Highly Enantioselective Direct Conjugate
Addition of a,a-Disubstituted Aldehydes to Nitroalkenes, Angew. Chem. Int.
Ed. 2006, 45, 63666370.
168.
Stevenson, C. P.;
Nielsen, L. P. C. Jacobsen, E. N. Preparation of (S)-Methyl Glycidate
via Hydrolytic Kinetic Resolution, Org. Synth. 2006, 83,
55, 162166.
169.
Yoon, T. P.; Jacobsen,
E. N. Arenecarboxylic Acids, Science of Synthesis 2006, 20a,
533549.
170.
Vanderwal, C. D.;
Jacobsen, E. N. Alk-2-enoic Acids, Science of Synthesis 2006, 20a,
551568.
171.
Yoon, T. P.; Jacobsen,
E. N. Arenecarboxylic Acid Esters, Science of Synthesis 2006, 20b,
12851304.
172.
Vanderwal, C. D.;
Jacobsen, E. N. Alk-2-enoic Acid Esters, Science of Synthesis 2006,
20b, 1305568.
173. Tan, K. L.; Jacobsen, E. N. Indium-Mediated
Asymmetric Allylation of Acylhydrazones Using a Chiral Urea Catalyst, Angew.
Chem. Int. Ed. 2007, 46, 13151317.
174. Doyle, A. G.; Jacobsen, E. N. Enantioselective Alkylation of Acyclic
a,a-Disubstituted Tributyltin Enolates
Catalyzed by a {Cr(salen)} Complex, Angew. Chem. Int. Ed.
2007, 46, 37013705.
175.
Balskus, E. P.; Jacobsen, E. N. Asymmetric Catalysis of the
Transannular DielsAlder Reaction, Science 2007, 317,
17361740.
176.
Raheem, I. T.; Thiara, P. V.; Peterson, E. A.; Jacobsen, E. N. Enantioselective
PictetSpengler-Type Cyclizations of Hydroxylactams: H-Bond Donor Catalysis by
Anion Binding, J. Am. Chem. Soc. 2007, 129, 1340413405.
177.
Zuend, S. J.; Jacobsen, E. N. "Cooperative Catalysis by Tertiary
Amino-Thioureas: Mechanism and Basis for Enantioselectivity of Ketone
Cyanosilylation," J. Am. Chem. Soc. 2007, 129, 1587215883.
178.
Doyle, A. G.; Jacobsen, E. N. Small-Molecule H-Bond Donors in
Asymmetric Catalysis," Chem. Rev. 2007, 107, 57135743.
179. Grachan, M. L.; Tudge, M. T.; Jacobsen, E. N. Enantioselective
Catalytic Carbonyl-ene Cyclization Reactions, Angew. Chem.,
Int. Ed. 2008, 47, 14691472.
180. Mazet,
C.; Jacobsen, E. N. Dimeric (salen)Al Complexes Display
Expanded Scope in the Conjugate Cyanation of a b-Unsaturated Imides, Angew. Chem.,
Int. Ed. 2008, 47, 17621765.
181. Mergott,
D. J.; Zuend, S. J.; Jacobsen, E. N. Catalytic Asymmetric Total Synthesis of
(+)-Yohimbine, Org. Lett. 2008, 10, 745748.
182. Belser,
T.; Jacobsen, E. N. Cooperative Catalysis in the Hydrolytic Kinetic Resolution
of Epoxides by chiral [(salen)CoIII] Complexes Immobilized on Gold
Colloids, Adv. Synth. Catal. 2008, 350, 967971.
183. Raheem,
I. T.; Thiara, P. V.; Jacobsen, E. N. Regio- and Enantioselective Cyclization
of Pyrroles onto N-Acyliminium Ions, Org. Lett. 2008, 10,
15771580.
184. Fang,
Y.-Q.; Jacobsen, E. N. Cooperative, Highly Enantioselective Phosphinothiourea
Catalysis of Imine-Allene [3+2] Cycloadditions, J. Am. Chem. Soc. 2008,
130, 56605661.
185. Reisman,
S. E.; Doyle, A. G.; Jacobsen, E. N. Enantioselective Thiourea-Catalyzed
Additions to Oxocarbenium Ions, J. Am. Chem. Soc. 2008, 130,
71987199.
186. Uyeda,
C.; Jacobsen, E. N. Enantioselective Claisen Rearrangements with a
Hydrogen-Bond Donor Catalyst, J. Am. Chem. Soc. 2008, 130,
92289229.
187. Watson,
M. P.; Jacobsen, E. N. Asymmetric Intramolecular Arylcyanation of Unactivated
Olefins via CCN Bond Activation, J. Am. Chem. Soc. 2008, 130,
1259412595.
188. Groll,
M.; Balskus, E. P.; Jacobsen, E. N., Structural Analysis of Spiro
β-Lactone Proteasome Inhibitors, J. Am. Chem. Soc. 2008, 130,
1498114983.
189. Klausen,
R. S.; Jacobsen, E. N. Weak Brønsted
Acid−Thiourea Co-catalysis: Enantioselective, Catalytic
Protio-Pictet−Spengler Reactions, Org.
Lett. 2009, 11, 887890.
190. Loy, Rebecca N.; Jacobsen, E. N. Enantioselective Intramolecular
Openings of Oxetanes Catalyzed by (salen)Co(III) Complexes: Access to
Enantioenriched Tetrahydrofurans, J. Am. Chem. Soc. 2009
131, 27862787.
191. Mita,
T.; Jacobsen, E. N. Bifunctional Asymmetric Catalysis with Hydrogen Chloride:
Enantioselective Ring Opening of Aziridines Catalyzed by a Phosphinothiourea, Synlett
2009, 16801684 (Special Cluster Issue on Cooperative Catalysis).
192. Peterson,
E. A.; Jacobsen, E. N. Enantioselective,
Thiourea-Catalyzed Intermolecular Addition of Indoles to Cyclic N-Acyl
Iminium Ions, Angew. Chem., Int. Ed. 2009, 48,
64466449.
193. Zuend,
S. J.; Coughlin, M. P.; Lalonde, M. P.; Jacobsen, E. N. Scaleable catalytic
asymmetric Strecker syntheses of unnatural a-amino
acids, Nature 2009, 461, 968970.
194. Zuend,
S. J., Jacobsen, E. N. Mechanism of Amido-Thiourea Catalyzed Enantioselective
Imine Hydrocyanation: Transition State Stabilization via Multiple Non-Covalent
Interactions, J. Am. Chem. Soc. 2009, 131, 1535815374.
195. Xu,
H.; Zuend, S. J.; Woll, M. P.; Tao, Y.; Jacobsen, E. N. Asymmetric Cooperative
Catalysis of Strong Brønsted Acid-Promoted Reactions Using Chiral Ureas, Science,
in press.