Si-free enolate Claisen rearrangements of enamido substrates?

Organic & Biomolecular Chemistry Pub Date: 2012-01-04 DOI: 10.1039/C2OB06853B

Abstract

α-Alkyl β-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 β-proline systems, is also presented.

Graphical abstract: Si-free enolate Claisen rearrangements of enamido substrates
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