Copper-Catalyzed Complete Regio- and Stereoselective Cyclization of 1-Aryl-3-sulfanyl-4-oxahepta-1,6-diynes Triggered by Alkynylation

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.

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Bibliographic Details
Published in:Organic letters 2012-06, Vol.14 (12), p.3190-3193
Main Authors: Yoshimatsu, Mitsuhiro, Sasaki, Hitomi, Sugimoto, Yuko, Nagase, Yuya, Tanabe, Genzoh, Muraoka, Osamu
Format: Article
Language:English
Subjects:
Alkylation
Catalysis
Copper - chemistry
Cyclization
Models, Molecular
Molecular Structure
Stereoisomerism
Sulfur Compounds - chemistry
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol3011453