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Synthesis 2001(11): 1716-1718
DOI: 10.1055/s-2001-16747
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© Georg Thieme Verlag Stuttgart · New York

Concise, Catalytic Asymmetric Synthesis of Tetrahydroisoquinoline- and Dihydroisoquinoline-3-carboxylic Acid Derivatives

Takashi Ooi, Mifune Takeuchi, Keiji Maruoka*
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan
Fax: +81(75)7534041; e-Mail: maruoka@kuchem.kyoto-u.ac.jp;
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Publication History

Received 6 April 2001
Publication Date:
28 September 2004 (online)

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Abstract

Catalytic asymmetric synthesis of tetrahydroisoquinoline-3-carboxylic acid (Tic) derivatives 1 has been accomplished by the successful utilization of phase-transfer catalysis of the C 2-symmetric chiral quaternary ammonium bromides. Our approach also enables facile synthesis of quaternary isoquinoline derivatives 2 and 3 with high enantiomeric purities.

Key words

alkylation - asymmetric synthesis - isoquinoline derivatives - phase-transfer catalysis - quaternary amino acids

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7

Absolute configuration (R) was confirmed by comparison of the optical rotation of 6 with the value of the tert-butyl ester of commercially available (S)-1,2,3,4-tetrahydroiso-quinoline-3-carboxylic acid.