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The sulfinyl moiety as an internal nucleophile. 2. Stereoselective synthesis of (-)-galantinic acid via 1,3-asymmetric induction.

作者信息

Raghavan Sadagopan, Reddy S Ramakrishna

机构信息

Organic Division I, Indian Institute of Chemical Technology, Hyderabad 500 007, India.

出版信息

J Org Chem. 2003 Jul 11;68(14):5754-7. doi: 10.1021/jo026892y.

DOI:10.1021/jo026892y
PMID:12839477
Abstract

A stereoselective synthesis of (-)-galantinic acid is disclosed. The key steps include hydrolytic kinetic resolution of a racemic epoxide and regio- and stereoselective heterofunctionalization of an olefin, using a pendant sulfinyl group as the nucleophile. The participation of the sulfinyl group was unambiguously proven by conducting the reaction in the presence of H(2)(18)O.

摘要

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