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

作者：Kissane Marie; Murphy Maureen; O'Brien Elisabeth; Chopra Jay; Murphy Linda; Collins Stuart G; Lawrence Simon E; Maguire Anita R^*

来源：Organic and Biomolecular Chemistry, 2011, 9(7): 2452-2472.

DOI：10.1039/c0ob00805b

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.

• 出版日期2011