Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Asymmetric Syntheses of β-Amino Acid and Aspartic Acid by Reformatsky Reaction
MITSURU FURUKAWATADASHI OKAWARAYOSHIHIDE NOGUCHIYURIKO TERAWAKI
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1978 Volume 26 Issue 1 Pages 260-263

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Abstract
Asymmetric syntheses of β-amino acids and aspartic acid were achieved by the reaction of optically active Schiff bases prepared from aldehydes and optically active amines, R (+)- and S (-)-α-methylbenzylamines, with Reformatsky reagents in the range of 18-28% optical purities. When the Schiff bases having R (+)-amino component were used in the reaction, (S)-β-amino acids and (R)-aspartic acid were formed. The use of the Schiff bases involving S (-)-amino component gave (R)-β-amino acids and (S)-aspartic acid. The reaction of Schiff bases prepared from aldehydes and benzylamine with optically active Reformatsky reagents having l-menthyl ester gave (S)-β-amino acids and (R)-aspartic acid in the range of 2-5% optical purities. The steric course were also presumed.
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© The Pharmaceutical Society of Japan
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