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Synthesis 1996; 1996(4): 475-482
DOI: 10.1055/s-1996-4237
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Direct Preparation of Allylstannanes from Allyl Alcohols: Convenient Synthesis of β-Substituted Allylstannanes and of Stereodefined γ-Substituted Allylstannanes

Stefan Weigand, Reinhard Brückner*
  • *Institut für Organische Chemie der Georg-August Universität, Tammannstr. 2, D-37077 Göttingen, Germany, Fax: +49(551)392944
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Publikationsdatum:
31. Dezember 2000 (online)

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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.

allyl alcohols - allylstannanes - stereoselectivity