Synthesis 2004(9): 1419-1428  
DOI: 10.1055/s-2004-822402
PAPER
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Synthesis of Substituted 3-Quinolyl Alkanols and Their Application to Asymmetric Autocatalysis

Itaru Sato, Tomohiko Nakao, Rie Sugie, Tsuneomi Kawasaki, Kenso Soai*
Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo, 162-8601, Japan
Fax: +81(3)32352214; e-Mail: soai@rs.kagu.tus.ac.jp;
Further Information

Publication History

Received 27 April 2004
Publication Date:
08 June 2004 (online)

Abstract

Enantioenriched 3-quinolyl alkanols act as asymmetric autocatalysts in the addition of diisopropylzinc to the corresponding substituted quinoline-3-carbaldehydes, to afford themselves with an amplified enantiomeric excess (ee) of up to 97%.