Double diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements.

Autor: Davies SG; The Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford, UK OX1 3QY. steve.davies@chemistry.ox.ac.uk, Garner AC, Nicholson RL, Osborne J, Savory ED, Smith AD
Jazyk: angličtina
Zdroj: Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2003 Sep 07 (17), pp. 2134-5.
DOI: 10.1039/b306323m
Abstrakt: 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.
Databáze: MEDLINE