Tetrahedron letters

Conjugate addition of (trimethylstannyl) copper reagents to α, β-acetylenic N, N-dimethylamides. Trapping of the intermediates with electrophiles

E Piers, JM Chong, BA Keay

Index: Piers, Edward; Chong, J. Michael; Keay, Brian A. Tetrahedron Letters, 1985 , vol. 26, # 51 p. 6265 - 6268

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Citation Number: 25

Abstract

A study of the reaction of Me 3 SnCu·.Me 2 S (1) and [Me 3 SnCuSPh]Li (2) with α,β - acetylenic N,N-dimethylamides 3 shows (a) that the overall process can be controlled experimentally so as to produce either N,N-dimethyl ( )-(4) or ( )-3-trimethylstannyl-2-alkenamides (5), (b) that the initially formed intermediate derived from interaction of 2 and 3 is significantly more stable than that obtained by reaction of 2 and α,β-acetylenic esters, and (c) that the intermediate ...