Direct preparation of allylstannanes from allyl alcohols: Convenient synthesis of β-substituted allylstannanes and of stereodefined γ-substituted allylstannanes

Article abstract of DOI:10.1055/s-1996-4237

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.