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Report | Regular issue | Vol 23, No. 2, 1985, pp.395-398
Published online, 1st January, 1970
DOI: 10.3987/R-1985-02-0395
An Enantioselective Synthesis of 1-(α-Hydroxyalkyl)-1,2,3,4-tetrahydroisoquinolines through Optically Active N-Oxaacyliminium Ion Intermediates

Shinzo Kano,* Yoko Yuasa, and Shiroshi Shibuya

*School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan

Abstract

An enantioselective synthesis of 1S-(1’S-hydroxyethyl)-. 1S-(1’S-hydroxybenzyl)- and 1R-(1’R-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline was achieved by reductive cleavage of the oxazolidinone ring of the corresponding 1-substituted oxazolo[4,3-a]isoquinolines, prepared by an application of N-oxaacyliminium ion cyclization with enantioselectivity.