DIRECT PREPARATION OF ALLYLSTANNANES FROM ALLYL ALCOHOLS - CONVENIENTSYNTHESIS OF BETA-SUBSTITUTED ALLYLSTANNANES AND OF STEREODEFINED GAMMA-SUBSTITUTED ALLYLSTANNANES

Authors
WEIGAND S BRUCKNER R
Citation
S. Weigand et R. Bruckner, DIRECT PREPARATION OF ALLYLSTANNANES FROM ALLYL ALCOHOLS - CONVENIENTSYNTHESIS OF BETA-SUBSTITUTED ALLYLSTANNANES AND OF STEREODEFINED GAMMA-SUBSTITUTED ALLYLSTANNANES, Synthesis, (4), 1996, pp. 475
Citations number
38
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Issue
4
Year of publication
1996
Database
ISI
SICI code
0039-7881(1996):4<475:DPOAFA>2.0.ZU;2-1
Abstract
Primary allyl alcohols are converted into allyltributylstannanes in a one-pot operation. It entails (i) deprotonation with BuLi, (ii) sulfon ylation with mesyl chloride, and (iii) nucleophilic substitution by Li SnBu(3). Conversions are quantitative with isolated yields ranging fro m 70 % to 100 %. If the starting allyl alcohol contains a stereogenic double bond its configuration is retained.