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

doi:10.1055/s-2007-1000932

PAPER

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;

Abstract

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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.

Keywords

Prins cyclization - phosphomolybdic acid - heteropoly acid - homoallyl alcohol - tetrahydropyran-4-ols

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