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Enantioselective Addition of Dialkylzinc to Aromatic Aldimines Mediated by Camphor-Derived Chiral β-Amino Alcohols
Journal article

Enantioselective Addition of Dialkylzinc to Aromatic Aldimines Mediated by Camphor-Derived Chiral β-Amino Alcohols

Wei-Ming Huang and Biing-Jiun Uang
Chemistry - An Asian Journal
2014

Abstract

Achiral additive Aldimine Dialkylzinc Enantioselective addition Synthetic methods -amino alcohol
The enantioselective addition of diethylzinc or dimethylzinc to N-(diphenylphosphinoyl)imines mediated by 1 or 2 could be achieved in high yields (70-97%) and enantioselectivities (85-98% ee). The catalytic loading of 1 or 2a could be reduced to 10mol% for methylation or ethylation of imines in high yields and enantioselectivities (79-96%) when the reaction was conducted in the presence of 1.8equiv of methanol. N-Monosubstituted amino alcohols induced higher enantioselectivity than their N,N-disubstituted congener in our catalytic system.

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