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Diastereoselective AzaBaylis–Hillman Reactions: Synthesis of Chiral αAllenylamines and 2Azetines from Allenic Esters

Authors :
Santos, Bruna S.
Cardoso, Ana L.
Matos Beja, Ana
Ramos Silva, Manuela
Paixão, José A.
Palacios, Francisco
Pinho e Melo, Teresa M. V. D.
Source :
European Journal of Organic Chemistry; June 2010, Vol. 2010 Issue: 17 p3249-3256, 8p
Publication Year :
2010

Abstract

The reactivity of allenic esters towards activated Nsulfonylimines in the presence of DABCO was explored. A formal [2+2] cycloaddition of benzyl buta2,3dienoate and Narylidenebenzenesulfonamides yielded mainly 2methyleneazetidines. Interestingly, a DABCOcatalysed reaction of 2,3allenoates, bearing a chiral auxiliary on the ester moiety, with Narylidenebenzenesulfonamides led to optically active azaBaylis–Hillman products and 2azetine derivatives.

Details

Language :
English
ISSN :
1434193X and 10990690
Volume :
2010
Issue :
17
Database :
Supplemental Index
Journal :
European Journal of Organic Chemistry
Publication Type :
Periodical
Accession number :
ejs21807783
Full Text :
https://doi.org/10.1002/ejoc.200901415