5-Exocyclic Products, 2,3,5-Trisubstituted Tetrahydrofurans via Prins-Type Cyclization

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...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 8; no. 16; pp. 3617 - 3619
Main Authors Chavre, Satish N, Choo, Hyunah, Cha, Joo Hwan, Pae, Ae Nim, Choi, Kyung Il, Cho, Yong Seo
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.08.2006
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
STEREOCONTROLLED PREPARATION
ACID
EPIMERIZATION
SUPPRESSION
TETRAHYDROPYRAN
Online AccessGet full text

Cover

More Information
Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol061528x