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

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

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

20 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)2134-2135
Number of pages2
JournalChemical Communications
Volume3
Issue number17
DOIs
Publication statusPublished - 1 Jan 2003

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