Highly Selective Synthesis of Tetrahydropyranes by Prins-cyclization Mediated by Tin(Ⅳ) Chloride

Abstract

Abstract: Recently, Prins-cyclization has been widely used to synthesize tetrahydropyrane derivatives, but allyl transferring and side chain exchange will take place during the process, and the yields of the expected tetrahydropyrans were poor. In this paper, we report a new route to prepare 2,4,6-trisubstituted tetrahydropyranes with a high selectivity and excellent yields by previously coordinating aldehyde with tin(Ⅳ) chloride, then adding homo-allyl alcohol drop by drop.

Key words: Highly selective Prins-cyclization, Tin(Ⅳ) chloride, Tetrahydropyranes

CLC Number:

O626

TrendMD:

WEN Mei-Jiao, CHANG Wei-Xing, LI Jing . Highly Selective Synthesis of Tetrahydropyranes by Prins-cyclization Mediated by Tin(Ⅳ) Chloride[J]. Chem. J. Chinese Universities, 2005, 26(3): 452.

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Highly Selective Synthesis of Tetrahydropyranes by Prins-cyclization Mediated by Tin(Ⅳ) Chloride

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