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: yadavpubiict.res.in
J. S. Yadav, B. V. S. Reddy, G. G. K. S. N. Kumar, S. Aravind, Synthesis, 2008, 395-400.
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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J. S. Yadav, B. V. S. Reddy, M. S. Reddy, N. Niranjan, A. R. Prasad, Eur. J. Org. Chem., 2003, 1779-1783.