Reactions of methylcopper and chiral organocuprates with 1-nitro-2-phenylethene and of lithium dimethylcuprate with methyl 3(nitrophenyl)propenoates

Organocopper compounds like methylcopper, lithium dimethylcuprate, chiral lithium methyl-(S)-2(1-dimethylaminoethyl)-phenylcuprate and lithium menthoxy(methyl)cuprate react with 1-nitro-2-phenylethene to give the conjugate addition product 1-nitro-2-phenylpropane in moderate yields. In the reaction with lithium methyl-(S)-2(1-dimethylaminoethyl)phenylcuprate 2% asymmetric induction was obtained. The reaction between lithium dimethylcuprate and methyl 3(4-nitrophenyl)propenoate gave the corresponding azoxy compound and no conjugate addition product, while methyl 3(3-nitrophenyl)propenoate gave some conjugate addition.