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