Copper-catalyzed conjugate additions of organozirconocenes. Synthetic and mechanistic studies.

P Wipf, W Xu, JH Smitrovich, R Lehmann, LM Venanzi

Index: Wipf, Peter; Xu, Wenjing; Smitrovich, Jacqueline H.; Lehmann, Roman; Venanzi, Luigi M. Tetrahedron, 1994 , vol. 50, # 7 p. 1935 - 1954

Full Text: HTML

Citation Number: 57

Abstract

In the presence of 3–10 mol% of Cu (l) salts such as CuBr· S Me2 or CuCN, alkylzirconocenes add readily to α, β-unsaturated ketones, aldehydes, and sulfones. The reaction yield is sensitive to the presence of Lewis acids and bases. Steric hindrance as well as a broad range of functional groups are tolerated in the conjugate addition process. Unsaturated N-acyl oxazolidinones give high diastereoselectivities for the formation of the ...