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Brønsted Acid-Mediated Stereoselective Cascade Construction of Functionalized Tetrahydropyrans from 2-(Arylmethylene)cyclopropylcarbinols and Aldehydes

Guo-Qiang Tian and Min Shi*

*State Key Laboratory of Organometallic Chenistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai, China, 200032, Email: mshimail.sioc.ac.cn

G.-Q. Tian, M. Shi, Org. Lett., 2007, 9, 2405-2408.

DOI: 10.1021/ol0709026 (free Supporting Information)


Abstract

2-(Arylmethylene)cyclopropylcarbinols could be converted to the corresponding tetrahydropyrans stereoselectively in the presence of Brønsted acids under mild conditions. A plausible Prins-type reaction mechanism has been proposed.

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proposed mechanism



Key Words

Tetrahydropyrans, Prins Reaction


ID: J54-Y2007-1910