Synthesis 2010(20): 3474-3480  
DOI: 10.1055/s-0030-1258204
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Tetrahydroisoquinolines via Cascade Reductive Amination of Isochromenylium Tetrafluoroborate with Primary Amines

Hong-Ze Liaoa, Zhi-Long Hub, Kai Cuib, Jiao Jiaob, Yong Qina, Zhu-Jun Yao*b
a Department of Chemistry of Medicinal Natural Products and Key Laboratory of Drug Targeting, West China School of Pharmacy, and State Key Laboratory of Biotherapy, Sichuan University, Chengdu, Sichuan 610041, P. R. of China
b State Key Laboratory of Bioorganic and Natural Products Chemistry and e-Institute of Chemical Biology of Shanghai Universities, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, 345 Lingling Road, Shanghai 200032, P. R. of China
e-Mail: yaoz@sioc.ac.cn;
Further Information

Publication History

Received 28 May 2010
Publication Date:
13 August 2010 (online)

Abstract

Reactions of isochromenylium tetrafluoroborates with various primary amines have been investigated under reductive amination conditions. The established cascade methodology provides a convenient one-step synthesis of various tetrahydroisoquinoline derivatives under mild conditions.

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Two diastereomeric isomers were observed in ¹³C NMR spectrum of 4c (all carbon peaks are reported in the experimental section), but they were homogeneous in the ¹H NMR spectrum.