Issue 66, 2014

Regio and stereoselective synthesis of β-keto functionalized C-glycosides via iron catalyzed Ferrier rearrangement reactions

Abstract

An efficient iron-catalyzed decarboxylative C-glycosylation of glycals with β-keto acids via decarboxylative Ferrier rearrangement reaction has been established. This approach provides a wide range of β-keto-functionalized 2,3-unsaturated C-glycosides in moderate to good yields. Good selectivities are mainly observed with the use of D-galactal along with bulkier β-keto acids bearing phenyl moieties.

Graphical abstract: Regio and stereoselective synthesis of β-keto functionalized C-glycosides via iron catalyzed Ferrier rearrangement reactions

Supplementary files

Article information

Article type
Paper
Submitted
22 Jul 2014
Accepted
31 Jul 2014
First published
12 Aug 2014

RSC Adv., 2014,4, 34816-34822

Author version available

Regio and stereoselective synthesis of β-keto functionalized C-glycosides via iron catalyzed Ferrier rearrangement reactions

H. Y. Tan, S. Xiang, W. L. Leng and X. Liu, RSC Adv., 2014, 4, 34816 DOI: 10.1039/C4RA07429G

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