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A novel stereoselective synthesis of (2Z)-2-arylsulfanylallylic alcohols by tin–lithium exchange of (E)-α-stannylvinyl sulfides

✍ Scribed by Yaping Xu; Wenyan Hao; Dong Wang; Mingzhong Cai

Publisher: John Wiley and Sons
Year: 2008
Tongue: English
Weight: 97 KB
Volume: 19
Category: Article
ISSN: 1042-7163
DOI: 10.1002/hc.20487

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✦ Synopsis

Abstract

Tin–lithium exchange reaction of (E)‐α‐stannylvinyl sulfides 1 with n‐butyllithium gave (Z)‐α‐arylsulfanylvinyllithiums 2, which reacted with aldehydes or ketones 3 to afford stereoselectively (2__Z__)‐2‐arylsulfanylallylic alcohols 4 in good to high yields. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:639–643, 2008; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20487

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