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Paper | Regular issue | Vol 48, No. 1, 1998, pp.139-144
Published online, 1st January, 1970
DOI: 10.3987/COM-97-8024
Asymmetric Synthesis of 3-Quinolylalkylamine by Enantioselective Alkylation of N-Diphenylphosphinyl-3-quinolylimine Using Chiral β-Amino Alcohols

Tadakatsu Hayase, Shunji Osanai, Takanori Shibata, and Kenso Soai*

*Department of Applied Chemistry, Faculty of Science, Science University of Tokyo, Kagurazaka 1-3, Shinjuku-ku, Tokyo 162-8601, Japan

Abstract

Chiral N-diphenylphosphinyl-3-quinolylamies (DPP amines) with up to 74.9% e.e. were obtained by the enantioselective alkylation using dialkylzincs in the presence of various chiral amino alcohols. The acidic hydrolysis of the chiral DPP amine afforded optically active chiral 3-quinolylamine without racemization.