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Paper | Regular issue | Vol 81, No. 12, 2010, pp.2781-2792
Published online, 25th October, 2010
DOI: 10.3987/COM-10-12055
Asymmetric Acyl-Strecker Reaction Promoted by Novel Thiourea Organocatalyst

Takuya Kanemitsu, Eisuke Toyoshima, Michiko Miyazaki, Kazuhiro Nagata, and Takashi Itoh*

*School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan

Abstract

Asymmetric acyl-Strecker reaction using novel thiourea organocatalyst is described. Screening experiments of the catalysts revealed that a bifunctional organocatalyst afforded an enantio-enriched product via an unique mechanism. That is, dihydroisoquinoline derivatives were converted to a corresponding 1-cyano-1,2,3,4-tetrahydroisoquinolines using the bifunctional thiourea catalyst derived from Betti base in moderate yield and enantioselectivity.