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

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.