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KMID : 1059519880320060588
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Journal of the Korean Chemical Society
1988 Volume.32 No. 6 p.588 ~ p.592
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A Highly Stereoselective Reaction in Aminolysis of 3-Acyl-4-(S)-isopropyl-1,3-thiazolidine-2-thione with Racemic Amines
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Jeong Tae-Myeong
Park Ki-Hun
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Abstract
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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.
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KEYWORD
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