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Issue 12, 2009
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Doubly diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements

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Abstract

The doubly diastereoselective [3,3]-sigmatropic aza-Claisen rearrangement of silylketene aminals derived from 5-substituted (3S,4ER)-1-benzyloxy-3-[N-acyl-N-(α-methylbenzyl)amino]pent-4-enes furnishes 2,3-disubstituted (R)-N-α-methylbenzyl (2S,3R,4E)-7-benzyloxyhept-4-enamides in >90% de under the “matched” control of both stereogenic centres. Rearrangement of the “mismatched” diastereomeric (3R,4ER)-substrates proceeds with low diastereoselectivity. The substrate scope of the doubly diastereoselective rearrangement of the “matched” substrates in which two new stereogenic centres are created has been delineated.

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

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Publication details

The article was received on 10 Feb 2009, accepted on 16 Mar 2009 and first published on 28 Apr 2009


Article type: Paper
DOI: 10.1039/B902753J
Citation: Org. Biomol. Chem., 2009,7, 2604-2611
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    Doubly diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements

    S. G. Davies, A. C. Garner, R. L. Nicholson, J. Osborne, P. M. Roberts, E. D. Savory, A. D. Smith and J. E. Thomson, Org. Biomol. Chem., 2009, 7, 2604
    DOI: 10.1039/B902753J

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