Issue 12, 2020

Palladium(ii)-catalyzed stereoselective synthesis of C-glycosides from glycals with diaryliodonium salts

Abstract

An efficient palladium(II) mediated C-glycosylation of glycals with diaryliodonium salts is described, providing a new strategy for the synthesis of 2,3-dideoxy C-aryl glycosides with excellent stereoselectivity. The C-glycosylation of a diverse range of glycals, including D-glucal, D-galactal, D-allal, L-rhamnal, L-fucal, L-arabinal, D-maltal, and D-lactal, occurred effectively and the corresponding C-glycosides were obtained in moderate to good yields. This protocol is commended as a significant addition to the field of carbohydrate chemistry due to the rich functional group compatibility, broad range of substrate scope and exceptional α-stereoselectivity.

Graphical abstract: Palladium(ii)-catalyzed stereoselective synthesis of C-glycosides from glycals with diaryliodonium salts

Supplementary files

Article information

Article type
Paper
Submitted
05 Feb 2020
Accepted
04 Mar 2020
First published
11 Mar 2020

Org. Biomol. Chem., 2020,18, 2242-2251

Palladium(II)-catalyzed stereoselective synthesis of C-glycosides from glycals with diaryliodonium salts

K. B. Pal, J. Lee, M. Das and X. Liu, Org. Biomol. Chem., 2020, 18, 2242 DOI: 10.1039/D0OB00247J

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