Organic Chemistry Portal



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:

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

DOI: 10.1021/ol0709026 (free Supporting Information)


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.

see article for more examples

proposed mechanism

Key Words

Tetrahydropyrans, Prins Reaction

ID: J54-Y2007-1910