Enantioselective Catalytic Addition of HCN to Ketoimines. Catalytic Synthesis of Quaternary Amino Acids
Top Cited Papers
- 24 February 2000
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 2 (6) , 867-870
- https://doi.org/10.1021/ol005636+
Abstract
Highly enantioselective addition of HCN to ketoimines has been achieved for the first time using readily accessible and recyclable Schiff base catalysts. Essentially quantitative isolated yield and enantioselectivity of up to 95% ee was obtained. Furthermore, some of the Strecker adducts could be recrystallized in high recovery, yielding optically pure materials. Conversion of the α-aminonitrile adducts to the corresponding α-quaternary α-amino acids was effected in high yield by a formylation/hydrolysis sequence.Keywords
This publication has 20 references indexed in Scilit:
- Enantioselective Allylations of Azlactones with Unsymmetrical Acyclic Allyl EstersJournal of the American Chemical Society, 1999
- Enantioselective Synthesis of α-Amino Nitriles from N-Benzhydryl Imines and HCN with a Chiral Bicyclic Guanidine as CatalystOrganic Letters, 1999
- Chiral Oxime Ethers in Asymmetric Synthesis. 3.1 Asymmetric Synthesis of (R)-N-Protected α-Amino Acids by the Addition of Organometallic Reagents to the ROPHy Oxime of CinnamaldehydeThe Journal of Organic Chemistry, 1999
- Ti-Catalyzed Enantioselective Addition of Cyanide to Imines. A Practical Synthesis of Optically Pure α-Amino AcidsJournal of the American Chemical Society, 1999
- Catalytic Asymmetric Allylation of Prochiral Nucleophiles, α-Acetamido-β-ketoestersJournal of the American Chemical Society, 1999
- Asymmetric Strecker-Type Reaction of α-Aryl Ketones. Synthesis of (S)-αM4CPG, (S)-MPPG, (S)-AIDA, and (S)-APICA, the Antagonists of Metabotropic Glutamate ReceptorsThe Journal of Organic Chemistry, 1998
- Schiff Base Catalysts for the Asymmetric Strecker Reaction Identified and Optimized from Parallel Synthetic LibrariesJournal of the American Chemical Society, 1998
- Asymmetric Catalysis of the Strecker Amino Acid Synthesis by a Cyclic DipeptideJournal of the American Chemical Society, 1996
- 3-Hydroxy-.alpha.-methyltyrosine progenitors, synthesis and evaluation of some (2-oxo-1,3-dioxol-4-yl)methyl estersJournal of Medicinal Chemistry, 1984
- Furfuryl FormateJournal of the American Chemical Society, 1942