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Highly stereoselective radical addition to 3-hydroxy-1-(methylthio)-1-(p-tolylsulfonyl)-1-alkenes and its application to the preparation of optically active compounds

✍ Scribed by Akio Kayano; Motohiro Akazome; Makoto Fujita; Katsuyuki Ogura

Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 946 KB
Volume: 53
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(97)00545-0

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✦ Synopsis

Ettlcient 1.2-asymmetric induction was realized in the addition ot a l-hydroxyalkyl radical (R2(7-OIt) to 3-hydroxy-l-(methylthio)-l-Cp-tolylsulfonyl)-l-alkenes and their acetates (1): Irradiationot l and benzophenone in an 'alcohol (R2CHOH) gave an adduct (2) with a high syn selectivity. Optically active I is easily obtainable by means of Lipase PS..cataly~d transesteritication and, therebre, the present radical asymmetric induction provides a synthetic route leading to various chiral compounds.

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