Tetrahedron Letters

Chloroacetylenes as Michael acceptors. II. Direct ethynylation and vinylation of tertiary enolates.

AS Kende, P Fludzinski

Index: Kende, Andrew S.; Fludzinski, Pawel Tetrahedron Letters, 1982 , vol. 23, # 23 p. 2373 - 2376

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Citation Number: 12

Abstract

Abstract The reaction of ClC CCl, PhC CCl and PhSC CCl with a variety of tertiary enolates leads in 43–90% yields to α-chloroethynyl, α-phenylethynyl and α- thiophenylethynyl derivatives. The− C CCl group is smoothly converted to− C CH using copper powder in HOAc/THF, or is directly reduced (H 2/Lindlar catalyst) to the− CH CH 2 group, thus providing facile access to many α-ethynyl and α-vinyl ketones and esters.