Organic & Biomolecular Chemistry 2012-02-21

Si-free enolate Claisen rearrangements of enamido substrates.

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

Index: Org. Biomol. Chem. 10(7) , 1406-10, (2012)

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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.

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