Synthesis 2008(3): 395-400  
DOI: 10.1055/s-2007-1000932
PAPER
© Georg Thieme Verlag Stuttgart · New York

The ‘Aqueous’ Prins Cyclization: A Diastereoselective Synthesis of 4-Hydroxytetrahydropyran Derivatives

Jhillu S. Yadav*, Basi V. Subba Reddy, Gunda G. K. S. Narayana Kumar, Seema Aravind
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: +91(40)27160512; e-Mail: yadavpub@iict.res.in;
Further Information

Publication History

Received 14 September 2007
Publication Date:
10 January 2008 (online)

Abstract

Phosphomolybdic acid (H3PMo12O40, a heteropoly acid) is found to catalyze efficiently the Prins cyclization of homoallylic alcohols with aldehydes in water at room temperature to provide tetrahydropyran-4-ol derivatives in high yields with all cis-selectivity. Only cyclic ketones can give spirocyclic products. The use of phosphomolybdic acid in water makes this procedure simple, more convenient, cost-effective, and environmentally friendly.