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Issue 17, 2003
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Double diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements

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Abstract

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

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

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Publication details

The article was received on 03 Oct 2002, accepted on 04 Jun 2003 and first published on 24 Jul 2003


Article type: Communication
DOI: 10.1039/B306323M
Citation: Chem. Commun., 2003,0, 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, 0, 2134
    DOI: 10.1039/B306323M

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