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Ligand-Controlled Monoselective C-Aryl Glycoside Synthesis via Palladium-Catalyzed C-H Functionalization of N-Quinolyl Benzamides with 1-Iodoglycals.

Authors :
Liu M
Niu Y
Wu YF
Ye XS
Source :
Organic letters [Org Lett] 2016 Apr 15; Vol. 18 (8), pp. 1836-9. Date of Electronic Publication: 2016 Mar 30.
Publication Year :
2016

Abstract

A monoselective synthesis of aryl-C-Δ(1,2)-glycosides from 1-iodoglycals via palladium-catalyzed ortho-C-H activation of N-quinolyl benzamides has been developed. An amino acid derivative was used as a crucial ligand to improve the yield and monoselectivity of the coupling reaction. The utility of this protocol was demonstrated by a concise synthesis of key moieties of some natural products.

Details

Language :
English
ISSN :
1523-7052
Volume :
18
Issue :
8
Database :
MEDLINE
Journal :
Organic letters
Publication Type :
Academic Journal
Accession number :
27026362
Full Text :
https://doi.org/10.1021/acs.orglett.6b00566