Title:
ASYMMETRIC 1,4-REDUCTIONS OF AND 1,4-ADDITIONS TO ENOATES AND RELATED SYSTEMS
Document Type and Number:
WIPO Patent Application WO2001019761
Kind Code:
A3
Abstract:
One aspect of the present invention relates to methods for the transition-metal-catalyzed asymmetric 1,4-addition of a nucleophile, e.g., hydride, to cyclic and acyclic enoates and enones. In certain embodiments of the methods of the present invention, the transition metal catalyst consists essentially of copper and an asymmetric bidentate biphosphine ligand.
Inventors:
BUCHWALD STEPHEN L
APPELLA DANIEL H
MORITANI YASUNORI
SHINTANI RYO
JURKAUSKAS VALDAS
APPELLA DANIEL H
MORITANI YASUNORI
SHINTANI RYO
JURKAUSKAS VALDAS
Application Number:
PCT/US2000/025088
Publication Date:
November 22, 2001
Filing Date:
September 13, 2000
Export Citation:
Assignee:
MASSACHUSETTS INST TECHNOLOGY (US)
International Classes:
C07B53/00; C07B57/00; C07B61/00; C07C45/58; C07C45/62; C07C45/68; C07C45/78; C07C67/303; C07C67/347; C07C253/30; C07C255/33; (IPC1-7): C07B53/00; C07C67/303; C07C67/347; C07C45/62; C07B57/00; C07C253/30
Other References:
U. LEUTENEGGER: "Enantioselective reduction of alpha,beta-unsaturated carboxylates with NaBH4 and catalytic amounts of chiral cobalt semicorrin complexes", ANGEWANDTE CHEMIE INTERNATIONAL EDITION., vol. 28, no. 1, 1989, WEINHEIM DE, pages 60 - 61, XP002169652
V. MASSONNEAU: "Catalytic asymmetric syntheses II. Hydrogenation of alpha,beta-unsaturated ketones using chiral ruthenium complexes", JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol. 327, 1987, LAUSANNE CH, pages 269 - 273, XP002169653
A. ALEXAKIS: "Asymmetric conjugate addition of diethyl zinc to enones with chiral phosphine ligands", TETRAHEDRON: ASYMMETRY., vol. 8, no. 24, 1997, OXFORD GB, pages 3987 - 3990, XP004101182
M. KANAI: "Catalytic asymmetric conjugate addition of Grignard reagents mediated by copper(I)-chiral bidentate phosphine complex", TETRAHEDRON LETTERS, vol. 36, no. 24, 1995, OXFORD GB, pages 4275 - 4278, XP004027968
B. H. LIPSHUTZ: "A convenient, efficient method for conjugate reductions using catalytic quantities of Cu(I)", TETRAHEDRON LETTERS, vol. 39, 1998, OXFORD GB, pages 4627 - 4630, XP002169654
D. H. APPELLA: "Asymmetric conjugate reduction of alpha,beta-unsaturated esters using a chiral phosphine-copper catalyst", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 121, no. 40, 13 October 1999 (1999-10-13), DC US, pages 9473 - 9474, XP002169655
V. MASSONNEAU: "Catalytic asymmetric syntheses II. Hydrogenation of alpha,beta-unsaturated ketones using chiral ruthenium complexes", JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol. 327, 1987, LAUSANNE CH, pages 269 - 273, XP002169653
A. ALEXAKIS: "Asymmetric conjugate addition of diethyl zinc to enones with chiral phosphine ligands", TETRAHEDRON: ASYMMETRY., vol. 8, no. 24, 1997, OXFORD GB, pages 3987 - 3990, XP004101182
M. KANAI: "Catalytic asymmetric conjugate addition of Grignard reagents mediated by copper(I)-chiral bidentate phosphine complex", TETRAHEDRON LETTERS, vol. 36, no. 24, 1995, OXFORD GB, pages 4275 - 4278, XP004027968
B. H. LIPSHUTZ: "A convenient, efficient method for conjugate reductions using catalytic quantities of Cu(I)", TETRAHEDRON LETTERS, vol. 39, 1998, OXFORD GB, pages 4627 - 4630, XP002169654
D. H. APPELLA: "Asymmetric conjugate reduction of alpha,beta-unsaturated esters using a chiral phosphine-copper catalyst", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 121, no. 40, 13 October 1999 (1999-10-13), DC US, pages 9473 - 9474, XP002169655
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