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Diastereoselective and Enantioselective Desymmetrization of α-Substituted Cyclohexadienones via Intramolecular Stetter Reaction

Diastereoselective and Enantioselective Desymmetrization of α-Substituted Cyclohexadienones via Intramolecular Stetter Reaction

Authors :
Shu-Li You
Minqiang Jia
Chuan Liu
Source :
The Journal of Organic Chemistry. 77:10996-11001
Publication Year :
2012
Publisher :
American Chemical Society (ACS), 2012.

Abstract

Highly diastereoselective and enantioselective desymmetrization of alpha-substituted cyclohexadienones via NHC-catalyzed intramolecular Stetter reaction was realized. Amino-indanol derived triazolium salt bearing a C6F5 group was found to be the optimal catalyst precursor in the intramolecular Stetter reaction furnishing tricyclic products bearing multi-stereocenters in up to 96% yield and >99% ee.

Details

ISSN :
15206904 and 00223263
Volume :
77
Database :
OpenAIRE
Journal :
The Journal of Organic Chemistry
Accession number :
edsair.doi.dedup.....3ca4080455488a25e209c8a6552e8a4a
Full Text :
https://doi.org/10.1021/jo3022555