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Synthesis 2008(17): 2733-2738  
DOI: 10.1055/s-2008-1067209
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Aluminum(III)-Promoted Prins Cyclization of 2-Allylphenols: An Expedient Synthesis of Benzoxepins

Jhillu S. Yadav*, Basi V. Subba Reddy, Nagendra Nath Yadav, Gujarathi Satheesh
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27160512; e-Mail: yadav@iict.res.in;
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Publication History

Received 8 April 2008
Publication Date:
06 August 2008 (online)

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Abstract

2-Allylphenols undergo smooth cross coupling with ketones under mild conditions to produce spirocyclic oxepins in good yields with high chemoselectivity, whereas aromatic aldehydes provide benzoxepins with moderate stereoselectivity. The use of aluminum(III) chloride makes this method simple, convenient, and cost effective.

Keywords

Prins cyclization - 2-allylphenols - carbonyl compounds - benzoxepins