Construction of Spirolactams by Unexpected Oxidative Cyclization of Alkenyl Diynes via Copper Catalysis

A copper-catalyzed oxidative cyclization of alkenyl N-propargyl ynamides is described. This protocol enables the practical synthesis of diverse spirocyclic γ-lactams bearing an exocyclic double bond with generally high Z/E selectivity in moderate to good yields. Importantly, this copper-catalyzed ox...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 25; no. 9; pp. 1525 - 1529
Main Authors Shi, Chong-Yang, Han, Tao, Hong, Feng-Lin, Ye, Long-Wu, Sun, Qing, Teng, Ming-Yu
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 10.03.2023
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
YNAMIDES
GOLD CATALYSIS
2H-PYRAN-3(6H)-ONES
CARBENES
CYCLOPROPANATION
OXIDATION/CYCLOPROPANATION
ACCESS
Online AccessGet full text

Cover

More Information
Summary:A copper-catalyzed oxidative cyclization of alkenyl N-propargyl ynamides is described. This protocol enables the practical synthesis of diverse spirocyclic γ-lactams bearing an exocyclic double bond with generally high Z/E selectivity in moderate to good yields. Importantly, this copper-catalyzed oxidative cyclization demonstrates a distinctive selectivity in comparison with the related gold catalysis.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.3c00319