Si-free enolate Claisen rearrangements of enamido substrates

Wesley R R Harker, E L Carswell, David R Carbery

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Abstract

alpha-Alkyl beta-amino esters are available in high diastereoselectivity through a silicon-free Claisen enolate [3,3]-sigmatropic rearrangement of enamide esters. Optimisation studies have probed the crucial role of the initial enolisation and the nature of the enamide N-centre. The demonstration of chirality transfer and the formation of beta-proline systems, is also presented.
Original languageEnglish
Pages (from-to)1406-1410
Number of pages5
JournalOrganic and Biomolecular Chemistry
Volume10
Issue number7
DOIs
Publication statusPublished - 2012

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