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
Org. Lett., 2007, 9 (12), pp 2405–2408
DOI: 10.1021/ol0709026
Publication Date (Web): May 16, 2007
Copyright © 2007 American Chemical Society

Abstract

Abstract Image

(E)- and (Z)-2-(Arylmethylene)cyclopropylcarbinols 1 could be converted to the corresponding tetrahydropyrans 2 and 3 stereoselectively in the presence of Brønsted acids MsOH or TsOH under mild conditions. A plausible Prins-type reaction mechanism has been proposed.

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History

  • Published In Issue June 07, 2007
  • Received April 20, 2007

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