Protecting group free, stereocontrolled synthesis of β-Halo-enamides

Pasqua, A.E., Crawford, J.J., Long, D.-L. and Marquez, R. (2012) Protecting group free, stereocontrolled synthesis of β-Halo-enamides. Journal of Organic Chemistry, 77(5), pp. 2149-2158. (doi: 10.1021/jo202130e)

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Publisher's URL: http://dx.doi.org/10.1021/jo202130e

Abstract

Enamides, dienamides, and enynamides are important building blocks in synthetic, biological, and medicinal chemistry as well as materials science. Despite the extensive breath of their potential utility in synthetic chemistry, there is a lack of simple, high-yielding methods to deliver them efficiently and as single isomers. In this paper, we present a novel, protecting group free, efficient, and stereoselective approach to the generation of β-halo-enamides. The methodology presented provides a robust synthetic platform from which E- or Z-enamides can be generated in good yields and with complete stereocontrol.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Marquez, Dr Rudi and Long, Dr Deliang
Authors: Pasqua, A.E., Crawford, J.J., Long, D.-L., and Marquez, R.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Journal of Organic Chemistry
Journal Abbr.:J. Org. Chem.
ISSN:0022-3263
ISSN (Online):1520-6904
Published Online:19 January 2012

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