Si-free enolate Claisen rearrangements of enamido substrates

Reference:

Harker, W. R. R., Carswell, E. L. and Carbery, D. R., 2012. Si-free enolate Claisen rearrangements of enamido substrates. Organic and Biomolecular Chemistry, 10 (7), pp. 1406-1410.

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Official URL:

http://dx.doi.org/10.1039/c2ob06853b

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.

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