An efficient DABCO-catalyzed Ireland-Claisen rearrangement of allylic acrylates

A novel DABCO-catalyzed Ireland-Claisen [3,3]-rearrangement of allylic acrylates to give alpha-methylene-gamma,delta-unsaturated carboxylic acids in the presence of an excess of TMSCl and DBU in refluxing acetonitrile was developed. The protocol provides an easy entry to alpha-methylene-gamma,delta-...

Full description

Saved in:
Bibliographic Details
Published inSynlett no. 2; pp. 288 - 292
Main Authors Li, Yunxia, Wang, Quanrui, Goeke, Andreas, Frater, Georg
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.02.2007
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
alpha-methylene-gamma,delta-unsaturated carboxylic acids
allylic acrylates
STEREOCHEMICAL CONTROL
Ireland-Claisen rearrangement
ESTERS
CONSTRUCTION
BAYLIS-HILLMAN REACTION
METHYLENE-GAMMA-BUTYROLACTONES
DABCO
Online AccessGet more information

Cover

More Information
Summary:A novel DABCO-catalyzed Ireland-Claisen [3,3]-rearrangement of allylic acrylates to give alpha-methylene-gamma,delta-unsaturated carboxylic acids in the presence of an excess of TMSCl and DBU in refluxing acetonitrile was developed. The protocol provides an easy entry to alpha-methylene-gamma,delta-unsaturated carboxylic acids from allylic alcohols in good yields.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2007-967985