5-Exocyclic products, 2,3,5-trisubstituted tetrahydrofurans via Prins-type cyclization

Satish N Chavre; Hyunah Choo; Joo Hwan Cha; Ae Nim Pae; Kyung Il Choi; Yong Seo Cho

doi:10.1021/ol061528x

5-Exocyclic products, 2,3,5-trisubstituted tetrahydrofurans via Prins-type cyclization

Org Lett. 2006 Aug 3;8(16):3617-9. doi: 10.1021/ol061528x.

Authors

Satish N Chavre¹, Hyunah Choo, Joo Hwan Cha, Ae Nim Pae, Kyung Il Choi, Yong Seo Cho

Affiliation

¹ Biochemicals Research Center, Korea Institute of Science and Technology, P.O. Box 131, Cheongryang, Seoul 130-650, Korea.

PMID: 16869674
DOI: 10.1021/ol061528x

Abstract

[reaction: see text] 5-Exocyclic products, 2,3,5-trisubstituted tetrahydrofurans, were synthesized from homopropargylic alcohols with terminally substituted alkynes and various aldehydes via Prins-type cyclization. It is of interest that the exocyclic vinyl cation generated as a result of Prins-type cyclization could be trapped as a vinyl triflate when CH2Cl2 was used as a solvent, whereas in ethereal solution the vinyl cation underwent hydrolysis to give the corresponding ketone product.