A convenient and efficient asymmetric synthesis of (S)-α-arylthiomethyl-α-hydroxybutyric acid esters

YY Kuang, FE Chen

Index: Kuang, Yun-Yan; Chen, Fen-Er Organic Preparations and Procedures International, 2005 , vol. 37, # 2 p. 184 - 188

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Citation Number: 8

Abstract

The synthetic route to 9a-b is depicted in Scheme I. Ethylmalonic acid (2), obtained by base hydrolysis of diethyl ethylmalonate, was subjected to a Mannich reaction2 with diethylamine and paraformaldehyde to produce 2-methylenebutyric acid (3) in 90% yield. 2- Methylenebutyryl chloride (4) was obtained in 55% yield along with 30% of 2-chloro-2- methylbutyryl chloride as an undesired by-product in the chlorination of 3, according to the ...

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