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Asymmetric conjugate addition of organometallic reagents to chiral alpha beta unsaturated esters



Asymmetric conjugate addition of organometallic reagents to chiral alpha beta unsaturated esters



Tetrahedron Asymmetry 2(5): 389-398



Asymmetric conjugate addition to .alpha.,b.beta.-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 diastereoslectivity in conjugate addition by organocuprates (R2CuLi) and/or Grignard reagents in the presence of copper iodide (RMgBr + CuI), respectively.

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