ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 32, Number 6
JKCSEZ 32(6)
December 20, 1988 

A chiral recognition was observed in aminolysis of 3-acyl-4(S)-isopropyl-1,3-thiazolidine-2-thione by racemic amine to give an optically active amide (S-excess) and amine (R-excess). This procedure can be applied to synthesis of macrocyclic diamide macrocyclic spermidine alkaloid, and peptide. The rate of this aminolysis is remarkably affected by steric surrounding; completion of reaction can be easily judged by the disappearance of the original yellow color of 4(S)-AITT. These features of the aminolysis suggested a potential recognition racemic amines by a chiral 4 (S)-AITT derivative. Thus 4 (S)-AITT was synthesized from 4 (S)-isopropyl-1, 3-thiazolidine-2-thione and carboxylic acids.