Direct Preparation of Allylstannanes from Allyl Alcohols: Convenient Synthesis of β-Substituted Allylstannanes and of Stereodefined γ-Substituted Allylstannanes
- 1 April 1996
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1996 (04) , 475-482
- https://doi.org/10.1055/s-1996-4237
Abstract
Primary allyl alcohols are converted into allyltributylstannanes in a one-pot operation. It entails (i) deprotonation with BuLi, (ii) sulfonylation with mesyl chloride, and (iii) nucleophilic substitution by LiSnBu3. Conversions are quantitative with isolated yields ranging from 70% to 100%. If the starting allyl alcohol contains a stereogenic double bond its configuration is retained.Keywords
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