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Davies SG, Garner AC, Nicholson RL, et al. Double diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements. Chem Commun (Camb). 2003;(17):2134-5doi: 10.1039/b306323m.
Davies, S. G., Garner, A. C., Nicholson, R. L., Osborne, J., Savory, E. D., & Smith, A. D. (2003). Double diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements. Chemical communications (Cambridge, England), (17), 2134-5. https://doi.org/10.1039/b306323m
Davies, Stephen G, et al. "Double diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements." Chemical communications (Cambridge, England) vol. ,17 (2003): 2134-5. doi: https://doi.org/10.1039/b306323m
Davies SG, Garner AC, Nicholson RL, Osborne J, Savory ED, Smith AD. Double diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements. Chem Commun (Camb). 2003 Sep 07;(17):2134-5. doi: 10.1039/b306323m. PMID: 13678167.
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Chem Commun (Camb). 2003 Sep 07;(17):2134-5. doi: 10.1039/b306323m.

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

Chemical communications (Cambridge, England)

Stephen G Davies, A Christopher Garner, Rebecca L Nicholson, James Osborne, Edward D Savory, Andrew D Smith

Affiliations

  1. The Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford, UK OX1 3QY. [email protected]

PMID: 13678167 DOI: 10.1039/b306323m

Abstract

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.

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