Highly Effective Chiral Ortho-Substituted BINAPO Ligands (o-BINAPO): Applications in Ru-Catalyzed Asymmetric Hydrogenations of β-Aryl-Substituted β-(Acylamino)acrylates and β-Keto Esters
- 12 April 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 124 (18), 4952-4953
- https://doi.org/10.1021/ja020121u
Abstract
A novel family of chiral ortho-substituted BINAPO ligands (o-BINAPO) were synthesized from BINOL, and their Ru complexes were highly efficient catalysts for asymmetric hydrogenation of β-aryl-substituted β-(acylamino)acrylates and β-aryl-substituted β-keto esters. The Ru-bisphosphinite catalysts can tolerate an E/Z mixture of β-aryl-substituted β-(acylamino)acrylates. These highly enantioselective hydrogenations provide a useful way to prepare β-aryl-substituted β-amino acids and β-hydroxyl acids.This publication has 29 references indexed in Scilit:
- Pressure Dependent Highly Enantioselective Hydrogenation of Unsaturated β-Amino Acid PrecursorsThe Journal of Organic Chemistry, 2001
- An Expedient Method for Resolution of 3-Amino-3-(3‘-pyridyl)propionic Acid and Related CompoundsOrganic Process Research & Development, 2000
- Highly Efficient Asymmetric Synthesis of β-Amino Acid Derivatives via Rhodium-Catalyzed Hydrogenation of β-(Acylamino)acrylatesThe Journal of Organic Chemistry, 1999
- The tert-Butanesulfinyl Group: An Ideal Chiral Directing Group and Boc-Surrogate for the Asymmetric Synthesis and Applications of β-Amino AcidsThe Journal of Organic Chemistry, 1998
- Chiral Lewis Acid Catalysis in Conjugate Additions of O-Benzylhydroxylamine to Unsaturated Amides. Enantioselective Synthesis of β-Amino Acid PrecursorsJournal of the American Chemical Society, 1998
- An Efficient Synthesis of (S)-(+)-Ethyl β-Amino-3-pyridinepropanoate Using Enantiopure SulfiniminesThe Journal of Organic Chemistry, 1996
- Asymmetric synthesis of homochiral syn- and anti-3-phenylisoserine derivatives: a practical strategy for the synthesis of the taxol C-13 side chainJournal of the Chemical Society, Perkin Transactions 1, 1993
- A practical, highly enantioselective synthesis of the taxol side chain via asymmetric catalysis.The Journal of Organic Chemistry, 1992
- Asymmetric Michael reactions of 3,5-dihydro-4H-dinaphth[2,1-c:1',2'-e]azepine with methyl crotonateThe Journal of Organic Chemistry, 1986
- Asymmetric syntheses of .BETA.-amino acids by the reduction of enamines.CHEMICAL & PHARMACEUTICAL BULLETIN, 1979