Preparation of multisubstituted enamides via rhodium-catalyzed carbozincation and hydrozincation of ynamides

Gourdet, B., Rudkin, M. E., Watts, C. A. and Lam, H. W. (2009) Preparation of multisubstituted enamides via rhodium-catalyzed carbozincation and hydrozincation of ynamides. Journal of Organic Chemistry, 74(20), pp. 7849-7858. (doi: 10.1021/jo901658v)

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Abstract

Rhodium-catalyzed carbozincation of ynamides using diorganozinc reagents or functionalized organozinc halides is described. Using a tri(2-furyl)phosphine-modified rhodium catalyst, the reaction course is altered to hydrozincation when diethylzinc is employed as the organozinc reagent. Trapping of the alkenylzinc intermediates produced in these reactions in further functionalization reactions is possible. Collectively, these processes enable access to a range of multisubstituted enamides in stereo- and regiocontrolled fashion.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Watts, Dr Ciorsdaidh
Authors: Gourdet, B., Rudkin, M. E., Watts, C. A., and Lam, H. W.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Journal of Organic Chemistry
Publisher:American Chemical Society
ISSN:0022-3263
ISSN (Online):1520-6904

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