Tetrahedron: Asymmetry

Asymmetric conjugate addition of organometallic reagents to chiral α, β-unsaturated esters

C Fang, T Ogawa, H Suemune, K Sakai

Index: Fang; Ogawa; Suemune; Sakai Tetrahedron Asymmetry, 1991 , vol. 2, # 5 p. 389 - 398

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Citation Number: 54

Abstract

Abstract Asymmetric conjugate addition to α, β-unsaturated ester was studied using four kinds of cyclic diols (1c–4c) as chiral auxiliaries. Among the tested substrates,(R, R)- cyclohexane-1, 2-diol derivatives (6a–c) and (1R, 2S)-2-hydroxymethylcyclopentanol derivative (7a) showed high and reverse diastereoselectivity in conjugate addition by organocuprates (R 2 CuLi) and/or Grignard reagents in the presence of copper iodide ( ...

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