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Issue 7, 2011
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Addition-substitution reactions of 2-thio-3-chloroacrylamides with carbon, nitrogen, oxygen, sulfur and selenium nucleophiles

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Abstract

Synthetically versatile conjugate addition of a range of carbon, nitrogen, oxygen, sulfur and selenium nucleophiles to the highly functionalised 2-thio-3-chloroacrylamides is described. The stereochemical and synthetic features of this transformation are discussed in detail. In most instances, the nucleophile replaces the chloro substituent with retention of stereochemistry. With the oxygen nucleophiles, a second addition can occur leading to acetals, while with the nitrogen nucleophiles, E-Z isomerism occurs in the resulting enamine derivatives. The ratio of the E/Z isomers can be rationalised on the basis of the substituent and the level of oxidation.

Graphical abstract: Addition-substitution reactions of 2-thio-3-chloroacrylamides with carbon, nitrogen, oxygen, sulfur and selenium nucleophiles

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Article information


Submitted
30 Sep 2010
Accepted
17 Dec 2010
First published
20 Dec 2010

Org. Biomol. Chem., 2011,9, 2452-2472
Article type
Paper

Addition-substitution reactions of 2-thio-3-chloroacrylamides with carbon, nitrogen, oxygen, sulfur and selenium nucleophiles

M. Kissane, M. Murphy, E. O'Brien, J. Chopra, L. Murphy, S. G. Collins, S. E. Lawrence and A. R. Maguire, Org. Biomol. Chem., 2011, 9, 2452
DOI: 10.1039/C0OB00805B

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