Copper-catalyzed complete regio- and stereoselective cyclization of 1-aryl-3-sulfanyl-4-oxahepta-1,6-diynes triggered by alkynylation

Mitsuhiro Yoshimatsu; Hitomi Sasaki; Yuko Sugimoto; Yuya Nagase; Genzoh Tanabe; Osamu Muraoka

doi:10.1021/ol3011453

Copper-catalyzed complete regio- and stereoselective cyclization of 1-aryl-3-sulfanyl-4-oxahepta-1,6-diynes triggered by alkynylation

Org Lett. 2012 Jun 15;14(12):3190-3. doi: 10.1021/ol3011453. Epub 2012 Jun 6.

Authors

Mitsuhiro Yoshimatsu¹, Hitomi Sasaki, Yuko Sugimoto, Yuya Nagase, Genzoh Tanabe, Osamu Muraoka

Affiliation

¹ Department of Chemistry, Faculty of Education, Gifu University, Yanagido 1-1, Japan. yoshimae@gifu-u.ac.jp

PMID: 22670873
DOI: 10.1021/ol3011453

Abstract

Copper(I)-catalyzed alkynylation-cyclization of 4-oxahepta-1,6-diynes 1 with a wide variety of terminal alkynes proceeded to give (3E,4Z)-3-(phenylsulfanylmethylene)-4-(2-propynylidene)tetrahydrofuran-2-yl]benzenes 2aa-he in high yields with complete regio- and stereoselectivity.

MeSH terms

Alkylation
Catalysis
Copper / chemistry*
Cyclization
Models, Molecular
Molecular Structure
Stereoisomerism
Sulfur Compounds / chemistry*

Substances

Sulfur Compounds
Copper