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KMID : 1059519890330040426
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Journal of the Korean Chemical Society
1989 Volume.33 No. 4 p.426 ~ p.430
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Highly Diastereoselective Aldol-Type Reaction Using 3-Acetylthiazolidine-2-thione
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Jeong Tae-Myeong
Park Ki-Hun
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Abstract
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Amino alcohol-derived thiazolidinethiones [4-(S)-IPTT, 4(S)-ETT] serve as efficient chiral auxiliary in tin medicated aldol condensation. A highly enantioselective aldol-type reaction forming various β-hydroxy carbonyl compounds from 3-acetylthiazolidine-2-thione and achiral aldehyde is achieved via divalent tin enolate. The other advantages of these chiral auxiliaries were the ease of removal by methanolysis.
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