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Double diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements.
- Source :
-
Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2003 Sep 07 (17), pp. 2134-5. - Publication Year :
- 2003
-
Abstract
- Asymmetric [3,3]-sigmatropic aza-Claisen rearrangement of the (Z)-N-allyl-N,O-silylketene aminal of (3S,4E,alphaR)-1-benzyloxy-3-(N-propionyl-N-alpha-methylbenzylamino)hex-4-ene furnishes (2S,3R,4E,alphaR)-N-alpha-methylbenzyl-2,3-dimethyl-7-benzyloxyhept-4-enamide in > 92% d.e.; rearrangement of the diastereomeric (3R,4E,alphaR)-(Z)-N,O-silylketene aminal proceeds with low diastereoselectivity.
Details
- Language :
- English
- ISSN :
- 1359-7345
- Issue :
- 17
- Database :
- MEDLINE
- Journal :
- Chemical communications (Cambridge, England)
- Publication Type :
- Academic Journal
- Accession number :
- 13678167
- Full Text :
- https://doi.org/10.1039/b306323m