Double diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements |
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| Authors: | Davies Stephen G Garner A Christopher Nicholson Rebecca L Osborne James Savory Edward D Smith Andrew D |
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| Affiliation: | The Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford, UK OX1 3QY. steve.davies@chemistry.ox.ac.uk |
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| 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. |
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