Issue 17, 2003
From the journal:

Chemical Communications

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

Stephen G. Davies,*a   A. Christopher Garner,a   Rebecca L. Nicholson,a   James Osborne,a   Edward D. Savorya  and  Andrew D. Smitha  

* Corresponding authors

a The Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford, UK
E-mail: steve.davies@chemistry.ox.ac.uk

Abstract

Asymmetric [3,3]-sigmatropic aza-Claisen rearrangement of the (Z)-N-allyl-N,O-silylketene aminal of (3S,4E,αR)-1-benzyloxy-3-(N-propionyl-N-α-methylbenzylamino)hex-4-ene furnishes (2S,3R,4E,αR)-N-α-methylbenzyl-2,3-dimethyl-7-benzyloxyhept-4-enamide in >92% d.e.; rearrangement of the diastereomeric (3R,4E,αR)-(Z)-N,O-silylketene aminal proceeds with low diastereoselectivity.

Graphical abstract: Double diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements

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Article information

DOI
https://doi.org/10.1039/B306323M
Article type
Communication
Submitted
03 Oct 2002
Accepted
04 Jun 2003
First published
24 Jul 2003

Chem. Commun., 2003, 2134-2135

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

S. G. Davies, A. C. Garner, R. L. Nicholson, J. Osborne, E. D. Savory and A. D. Smith, Chem. Commun., 2003, 2134 DOI: 10.1039/B306323M

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