Highly Diastereoselective Heterogeneously Catalyzed Hydrogenation of Enamines for the Synthesis of Chiral β-Amino Acid Derivatives
- 19 February 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 126 (10) , 3048-3049
- https://doi.org/10.1021/ja038812t
Abstract
Pure (Z)-enamines readily prepared from beta-ketoesters and amides using (S)-phenylglycine amide were hydrogenated with very high diastereoselectivities (up to 200:1) using heterogeneous catalysis. Hydrogenolytic cleavage of the (S)-phenylglycine amide afforded the corresponding chiral beta-aminoesters and amides. The high geometrical purity of the (Z)-enamine and a simple activation procedure for the PtO2 catalyst are essential in achieving high selectivity.Keywords
This publication has 18 references indexed in Scilit:
- A Bisphosphepine Ligand with Stereogenic Phosphorus Centers for the Practical Synthesis of β‐Aryl‐β‐Amino Acids by Asymmetric HydrogenationAngewandte Chemie International Edition in English, 2003
- Enantioselective Hydrogenation of Tetrasubstituted Olefins of Cyclic β-(Acylamino)acrylatesJournal of the American Chemical Society, 2003
- Chiral β-Amino Acid Derivatives via Asymmetric HydrogenationOrganic Process Research & Development, 2003
- Preparation and Asymmetric Hydrogenation of β‐Aryl‐Substituted β‐AcylaminoacrylatesAngewandte Chemie International Edition in English, 2003
- Ru-Catalyzed Highly Enantioselective Hydrogenation of β-Alkyl-Substituted β-(Acylamino)acrylatesThe Journal of Organic Chemistry, 2003
- 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 EstersJournal of the American Chemical Society, 2002
- Highly Efficient Asymmetric Synthesis of β-Amino Acid Derivatives via Rhodium-Catalyzed Hydrogenation of β-(Acylamino)acrylatesThe Journal of Organic Chemistry, 1999
- Asymmetric syntheses of .BETA.-amino acids by the reduction of enamines.CHEMICAL & PHARMACEUTICAL BULLETIN, 1979
- Platinum Oxide CatalystsJournal of the American Chemical Society, 1954
- Exchange reactions of hydrogen on metallic catalystsTransactions of the Faraday Society, 1934