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Synthesis 2008(3): 395-400
DOI: 10.1055/s-2007-1000932
DOI: 10.1055/s-2007-1000932
PAPER
© Georg Thieme Verlag Stuttgart · New YorkThe ‘Aqueous’ Prins Cyclization: A Diastereoselective Synthesis of 4-Hydroxytetrahydropyran Derivatives
Further Information
Received
14 September 2007
Publication Date:
10 January 2008 (online)
Publication History
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.
Keywords
Prins cyclization - phosphomolybdic acid - heteropoly acid - homoallyl alcohol - tetrahydropyran-4-ols
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