Remarkable Enhancement of Nucleophilicity of Tin Enolates toward Nitro- or Cyanoalkenes by Tetrabutylammonium Halides

The reaction of tin enolates with nitroalkenes was effectively catalyzed by tetrabutylammonium bromide (Bu4NBr) to give γ-nitroketones. When the substituted tin enolates at the β-carbon in the olefinic moiety were used, the diastereoselective addition proceeded through the acyclic transition state....

Full description

Saved in:
Bibliographic Details
Published in:Chemistry letters 2000-11, Vol.29 (11), p.1266-1267
Main Authors: Yasuda, Makoto, Ohigashi, Noriyuki, Baba, Akio
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The reaction of tin enolates with nitroalkenes was effectively catalyzed by tetrabutylammonium bromide (Bu4NBr) to give γ-nitroketones. When the substituted tin enolates at the β-carbon in the olefinic moiety were used, the diastereoselective addition proceeded through the acyclic transition state. Tetrabutylammonium chloride (Bu4NCl) strongly accelerated the reaction with the cyanoalkene to give the γ-cyanoketone.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.2000.1266