Direct asymmetric organocatalytic Michael reactions of α,α-disubstituted aldehydes with β-nitrostyrenes for the synthesis of quaternary carbon-containing products
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作者:
Mase, N
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机构:Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
Mase, N
Thayumanavan, R
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机构:Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
Thayumanavan, R
Tanaka, F
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机构:Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
Tanaka, F
Barbas, CF
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机构:Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
Barbas, CF
机构:
[1] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
[2] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
[3] Scripps Res Inst, Dept Mol Biol, La Jolla, CA 92037 USA
Direct asymmetric catalytic Michael reactions have been performed using chiral-amine/acid bifunctional catalysts. Performed with 0.3 equiv of (S)-(+)-1-(2-pyrrolidinylmethyl)pyrrolidine and 0.3 equiv of trifluoroacetic acid as the catalyst, the reaction of alpha,alpha-dialkylaldehydes with (E)-beta-nitrostyrene provided the alpha,alpha-dialkyl Michael products in up to 96% yield with up to 91% ee. With respect to enantioselectivity, L-proline was a poor catalyst of this class of Michael reactions.