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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, Email:

J. S. Yadav, B. V. S. Reddy, G. G. K. S. N. Kumar, S. Aravind, Synthesis, 2008, 395-400.

DOI: 10.1055/s-2007-1000932


Phosphomolybdic acid catalyzes 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. The use of phosphomolybdic acid in water makes this procedure simple, convenient, cost-effective, and environmentally friendly.

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Lewis Acidic Chloroaluminate Ionic Liquids: Novel Reaction Media for the Synthesis of 4-Chloropyrans

J. S. Yadav, B. V. S. Reddy, M. S. Reddy, N. Niranjan, A. R. Prasad, Eur. J. Org. Chem., 2003, 1779-1783.

Key Words

Prins reaction, phosphomolybdic acid, heteropoly acid, homoallyl alcohols, tetrahydropyran-4-ols, tetrahydropyrans, green chemistry

ID: J66-Y2008-0380