Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 1996; 1996(4): 475-482
DOI: 10.1055/s-1996-4237
DOI: 10.1055/s-1996-4237
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.
Direct Preparation of Allylstannanes from Allyl Alcohols: Convenient Synthesis of β-Substituted Allylstannanes and of Stereodefined γ-Substituted Allylstannanes
Further Information
Publication History
Publication Date:
31 December 2000 (online)
![](https://www.thieme-connect.de/media/synthesis/199604/lookinside/thumbnails/10.1055-s-1996-4237-1.jpg)
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