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Communication | Special issue | Vol 47, No. 1, 1998, pp.125-128
Published online, 1st January, 1970
DOI: 10.3987/COM-97-S(N)44
Synthesis of 1,2-Dihydroisoquinolines by the Reaction of Isoquinoline with Allyltributyltin or Silyl Enol Ethers in the Presence of N-Acylating Agents

Takashi Itoh, Michiko Miyazaki, Kazuhiro Nagata, Hiroshi Hasegawa, Akio Ohsawa,* and Kazuo T. Nakamura

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

Abstract

Isoquinolines were allowed to react with allyltributyltin or silyl enol ethers in the presence of N-acylating agents to give 1-substituted 1,2-dihydroisoquinolines in good yields. When a chiral acid chloride was used for an activator, a high diastereoselectivity was observed for the addition. The configuration of a major isomer was elucidated by an X-Ray crystallographic analysis.