Tetrahedron Asymmetry p. 389 - 398 (1991)
Update date:2022-08-05
Topics: Chiral Organometallic reagents Asymmetric Conjugate addition α,β-unsaturated esters Experimental
Fang
Ogawa
Suemune
Sakai
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 (R2CuLi) and/or Grignard reagents in the presence of copper iodide (RMgBr + CuI), respectively.
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