The'aqueous' Prins cyclization: a diastereoselective synthesis of 4-hydroxytetrahydropyran derivatives

Yadav, Jhillu S. ; Subba Reddy, Basi V. ; Narayana Kumar, Gunda G. K. S. ; Aravind, Seema (2008) The'aqueous' Prins cyclization: a diastereoselective synthesis of 4-hydroxytetrahydropyran derivatives Synthesis, 2008 (3). pp. 395-400. ISSN 0039-7881

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Official URL: http://www.thieme-connect.com/ejournals/abstract/s...

Related URL: http://dx.doi.org/10.1055/s-2007-1000932

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.

Item Type:Article
Source:Copyright of this article belongs to Thieme Medical Publishers.
Keywords:Prins Cyclization; Phosphomolybdic Acid; Heteropoly Acid; Homoallyl Alcohol; Tetrahydropyran-4-ols
ID Code:63107
Deposited On:28 Sep 2011 03:37
Last Modified:28 Sep 2011 03:37

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