A highly enantioselective rhodium catalyst for the hydrogenation of aliphatic α‐keto esters
- 1 January 1991
- Vol. 3 (4) , 370-375
- https://doi.org/10.1002/chir.530030423
Abstract
The enantioselective hydrogenation of several α‐keto acid derivatives with rhodium diphosphine catalysts has been investigated using a random screening approach. The neutral rhodium catalyst prepared in situ from bis(2,5‐norbornadiene rhodium chloride) and NORPHOS has been found to be an excellent catalyst for preparing aliphatic α‐hydroxy esters in high optical purities. The reaction parameters for the hydrogenation of ethyl 2‐oxo‐4‐phenyl‐butyrate, an intermediate for the ACE inhibitor Benazepril, were optimized and the best optical yields obtained were 96%.Keywords
This publication has 23 references indexed in Scilit:
- Asymmetric synthesis. Molecular graphics and enantioselection in asymmetric catalytic hydrogenationOrganometallics, 1989
- Notiz zur Synthese Eines Optisch Aktiven Ace‐Hemmers mit Amino‐oxo‐benzazepin‐1‐alkansäure‐Struktur mittels enantiokonvergierender kristallisationsinduzierter Racemat‐TrennungHelvetica Chimica Acta, 1988
- Correction. Asymmetric Hydrogenation of Methyl-(Z)-α-acetamidocinnamate Catalyzed by {1,2-Bis(phenyl-o-anisoyl)phosphino)ethane}rhodium(I): Kinetics, Mechanism and Origin of EnantioselectionJournal of the American Chemical Society, 1987
- Asymmetric hydrogenation of .beta.-keto carboxylic esters. A practical, purely chemical access to .beta.-hydroxy esters in high enantiomeric purityJournal of the American Chemical Society, 1987
- Highly Effective Catalytic Asymmetric Hydrogenations of α-Keto Esters and an α-Keto Acetal with New Neutral Chiral Pyrrolidinebisphosphine-Rhodium ComplexesChemistry Letters, 1987
- Asymmetric hydrogenation of methyl (Z)-.alpha.-acetamidocinnamate catalyzed by [1,2-bis(phenyl-o-anisoyl)phosphino)ethane]rhodium(I): kinetics, mechanism and origin of enantioselectionJournal of the American Chemical Society, 1987
- Chiral Compounds Synthesized by Biocatalytic Reductions [New Synthetic Methods (51)]Angewandte Chemie International Edition in English, 1985
- Remarkable optical induction in the reduction of .alpha.-oxo esters with B-(3-pinanyl)-9-borabicyclo[3.3.1]nonane. Synthesis of .alpha.-hydroxy esters of 100% optical purityJournal of the American Chemical Society, 1984
- Rhodium Catalysts for Enantioselective Hydrosilylation—A New Concept in the Development of Asymmetric CatalystsAngewandte Chemie International Edition in English, 1983
- Effective homogeneous hydrogenation of α-keto esters catalysed by neutral rhodium(I) complexes with phosphine ligands and application to the asymmetric synthesis of lactatesJournal of the Chemical Society, Chemical Communications, 1977