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Synthesis 2004(3): 405-408  
DOI: 10.1055/s-2004-815942
PAPER
© Georg Thieme Verlag Stuttgart · New York

InCl 3 -Catalyzed Tandem Michael/Friedel-Crafts Cyclization: A Novel Protocol for Chiral 2,4-Disubstituted Tetrahydroquinolines

J. S. Yadav*, B. V. S. Reddy, B. Padmavani
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad-500 007, India
Fax: +91(40)27160512; e-Mail: yadav@iict.ap.nic.in;
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Publication History

Received 1 December 2003
Publication Date:
03 February 2004 (online)

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Abstract

δ-Hydroxy-α,β-unsaturated aldehydes undergo a tandem Michael and intramolecular Friedel-Crafts type cyclization with arylamines in the presence of 10 mol% InCl3 under mild conditions to afford a novel class of optically active tetrahydroquinolines in good yields with high stereoselectivity. The stereochemistry of the products was determined using various NMR experiments.

Key words

arylamines - α,β-unsaturated aldehydes - benzo-fused heterobicycles

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Acyclic δ-hydroxy-α,β-unsaturated aldehyde was prepared from d-glucal using a known procedure reported in literature: Wengel J., Lau J., Pedersen E. B.; Synthesis; 1989, 829