Brønsted acid-mediated stereoselective cascade construction of functionalized tetrahydropyrans from 2-(arylmethylene)cyclopropylcarbinols and aldehydes.

Org Lett

State Key Laboratory of Organometallic Chenistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai, China.

Published: June 2007

(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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Source
http://dx.doi.org/10.1021/ol0709026DOI Listing

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