The 'Aqueous' Prins cyclization: A diastereoselective synthesis of 4-hydroxytetrahydropyran derivatives

被引：47
|
作者：
Yadav, Jhillu S. [1 ]
Reddy, Basi V. Subba [1 ]
Kumar, Gunda G. K. S. Narayana [1 ]
Aravind, Seema [1 ]
机构：
[1] Indian Inst Chem Technol, Div Organ Chem, Hyderabad 500007, Andhra Pradesh, India
来源：
SYNTHESIS-STUTTGART | 2008年 / 3卷 / 03期
关键词：
Prins cyclization; phosphomolybdic acid; heteropoly acid; homoallyl alcohol; tetrahydropyran-4-ols;
D O I：
10.1055/s-2007-1000932
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
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页码：395 / 400
页数：6
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