The Enantioselective Synthesis of α-Amino Acid Derivatives via Organoboranes

Optically active (S)-α-amino acids are prepared in 54−95% ee (12 cases) by reaction of the Schiff base acetate of glycine tert-butyl ester with B-alkyl-9-BBN derivatives in the presence of the Cinchona alkaloid, cinchonidine, and base. The enantiomeric (R)-α-amino acids are available in 59−92% ee (3...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2002-08, Vol.124 (32), p.9348-9349
Main Authors: O'Donnell, Martin J, Drew, Mark D, Cooper, Jeremy T, Delgado, Francisca, Zhou, Changyou
Format: Article
Language:English
Subjects:
Amino Acids - chemical synthesis
Amino Acids - chemistry
Boranes - chemistry
Chemistry
Exact sciences and technology
Kinetics and mechanisms
Organic chemistry
Organometallic Compounds - chemistry
Reactivity and mechanisms
Stereoisomerism
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Summary:Optically active (S)-α-amino acids are prepared in 54−95% ee (12 cases) by reaction of the Schiff base acetate of glycine tert-butyl ester with B-alkyl-9-BBN derivatives in the presence of the Cinchona alkaloid, cinchonidine, and base. The enantiomeric (R)-α-amino acids are available in 59−92% ee (3 cases) by using cinchonine as the chiral control element.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja017522e