Highly enantioselective alkylation of carbon–nitrogen double bonds. Catalytic and stoichiometric asymmetric synthesis of optically active amines by the enantioselective addition of dialkylzinc reagents to N-diphenylphosphinoylimines

Kenso Soai; Toshihiro Hatanaka; Tohru Miyazawa

doi:10.1039/C39920001097

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Highly enantioselective alkylation of carbon–nitrogen double bonds. Catalytic and stoichiometric asymmetric synthesis of optically active amines by the enantioselective addition of dialkylzinc reagents to N-diphenylphosphinoylimines

Kenso Soai, Toshihiro Hatanaka and Tohru Miyazawa

Abstract

The first highly enantioselective alkylation of carbon–nitrogen double bonds (of N-diphenylphosphinoylimines) with dialkylzinc reagents promoted by chiral amino alcohols afforded optically active phosphoramides (precursors of amines) in up to 91% enantiomeric excess.

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DOI: https://doi.org/10.1039/C39920001097
Article type: Paper

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J. Chem. Soc., Chem. Commun., 1992, 1097-1098

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Highly enantioselective alkylation of carbon–nitrogen double bonds. Catalytic and stoichiometric asymmetric synthesis of optically active amines by the enantioselective addition of dialkylzinc reagents to N-diphenylphosphinoylimines

K. Soai, T. Hatanaka and T. Miyazawa, J. Chem. Soc., Chem. Commun., 1992, 1097 DOI: 10.1039/C39920001097

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Journal of the Chemical Society, Chemical Communications

Highly enantioselective alkylation of carbon–nitrogen double bonds. Catalytic and stoichiometric asymmetric synthesis of optically active amines by the enantioselective addition of dialkylzinc reagents to N-diphenylphosphinoylimines

Abstract

Article information

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Highly enantioselective alkylation of carbon–nitrogen double bonds. Catalytic and stoichiometric asymmetric synthesis of optically active amines by the enantioselective addition of dialkylzinc reagents to N-diphenylphosphinoylimines

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