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

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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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Supplementary files

Article information

10 Feb 2009
16 Mar 2009
First published
28 Apr 2009

Org. Biomol. Chem., 2009,7, 2604-2611
Article type

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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