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Communication | Regular issue | Vol 63, No. 1, 2004, pp.17-22
Published online, 21st November, 2003
DOI: 10.3987/COM-03-9928
Synthesis of Optically Active Tetrahydro-3-benzazepine-2-carboxylic Acid Derivatives via the Ring Expansion Reaction of Isoquinolines and Enzymatic Resolution

Yuji Koseki, Hidefumi Ozawa, Katsuaki Kitahara, Ichiro Kato, Hiroto Sato, Haruhiko Fukaya, and Tatsuo Nagasaka*

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

Abstract

The facial approach to 3-benzazepine-2-carboxylic acid derivatives (1) via the ring expansion reactions of 10b-hydroxymethyloxazoloisoquinolines (3) to 3-benzazepines (2) is described. Utilizing enzymatic resolution, the synthesis of (-)-(S)-N-Cbz-3-benzazepine-2-carboxylic acid (1b) was achieved.