Highly Stereoselective Synthesis of the Anti-Platelet Activating Factor, 4-Thiazolidinones, Using Silyl Derivatives of 2-Mercaptoalkanoic Acids.

…, H Okumura, M Nagaosa, M Murakami

Index: Tanabe; Okumura; Nagaosa; Murakami Bulletin of the Chemical Society of Japan, 1995 , vol. 68, # 5 p. 1467 - 1472

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Citation Number: 13

Abstract

The cyclo-condensation of silyl 2-mercaptoalkanoates and arylmethyleneamines proceeded with high stereoselectivity to give alternatively both the cis-and trans-2, 5-disubstituted 4- thiazolidinones, some of which are known as anti-platelet activating factor-active drugs. The use of the piperidine catalyst and no catalyst showed very high cis-stereoselectivity (cis/trans= 10/1—50/1) during the reaction. On the other hand, the trans-selective reaction ...