Back to Search Start Over

Tandem Palladium-Catalyzed 6- exo- dig Oxocyclization Coupling of δ-Acetylenic β-Ketoesters with Aryl Bromides and Chlorides: Route to Substituted Dihydropyrans.

Authors :
Kołodziejczyk A
Domański S
Chaładaj W
Source :
The Journal of organic chemistry [J Org Chem] 2018 Oct 19; Vol. 83 (20), pp. 12887-12896. Date of Electronic Publication: 2018 Sep 28.
Publication Year :
2018

Abstract

We report an efficient and functional group-tolerant method for the synthesis of substituted dihydropyrans, based on tandem Pd-catalyzed cyclization/coupling of δ-acetylenic β-ketoesters with aryl halides. The reaction proceeds cleanly through 6- exo-dig oxocyclizaton mode, delivering products with very good yields and complete control of regio- and stereoselectivity. Due to mild conditions, the transformation offers exceptional tolerance of functionalities, including NHR, formyl, enolizable ketone, free OH and NH <subscript>2</subscript> groups, as well as a range of N-heterocyclic moieties of potential biological relevance.

Details

Language :
English
ISSN :
1520-6904
Volume :
83
Issue :
20
Database :
MEDLINE
Journal :
The Journal of organic chemistry
Publication Type :
Academic Journal
Accession number :
30204434
Full Text :
https://doi.org/10.1021/acs.joc.8b01832