Si-free enolate Claisen rearrangements of enamido substrates

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

doi:10.1039/c2ob06853b

Si-free enolate Claisen rearrangements of enamido substrates

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

9 Citations (SciVal)

352 Downloads (Pure)

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 language	English
Pages (from-to)	1406-1410
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	10
Issue number	7
DOIs	https://doi.org/10.1039/c2ob06853b
Publication status	Published - 2012

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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.",

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AU - Harker, Wesley R R

AU - Carswell, E L

AU - Carbery, David R

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N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/84856713172

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

U2 - 10.1039/c2ob06853b

DO - 10.1039/c2ob06853b

M3 - Article

SN - 1477-0520

VL - 10

SP - 1406

EP - 1410

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 7

ER -

Si-free enolate Claisen rearrangements of enamido substrates

Abstract

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