Organic Chemistry Portal



5- and 6-Exocyclic Products, cis-2,3,5-Trisubstituted Tetrahydrofurans, and cis-2,3,6-Trisubstituted Tetrahydropyrans via Prins-Type Cyclization

Satish N. Chavre, Hyunah Choo, Jae Kyun Lee, Ae Nim Pae, Youseung Kim and Yong Seo Cho*

*Center for Chemoinformatics Research, Korea Institute of Science and Technology, P.O. Box 131, Cheongryang, Seoul 130-650, Korea, Email:

S. N. Chavre, H. Choo, J. K. Lee, A. N. Pae, Y. Kim, Y. S. Cho, J. Org. Chem., 2008, 73, 7467-7471.

DOI: 10.1021/jo800967p


Exo-3-furanylidenes and 3-pyranylidenes products having cis-2,5 and cis-2,6 substitution were synthesized from terminally substituted alkynyl alcohols with various aldehydes via Prins-type cyclization and trapping of the resulting vinyl cations as vinyl triflates in good yields. Vinyl triflates underwent a subsequent stereoselective hydrolysis to give the corresponding 3-acyl-substituted products.

see article for more examples

see article for more reactions

see article for more examples

proposed mechanism

Key Words

Tetrahydrofurans, Tetrahydropyrans, Prins Reaction, Hydrolysis

ID: J42-Y2008-2670