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Double diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements
Stephen G Davies1, A Christopher Garner, Rebecca L Nicholson
1The Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford, UK OX1 3QY. steve.davies@chemistry.ox.ac.uk
Chemical Communications (Cambridge, England)
|September 19, 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.