Regio and stereoselective synthesis of β-keto functionalized C-glycosides via iron catalyzed Ferrier rearrangement reactions†
Hong Yee Tan,Shaohua Xiang,Wei Lin Leng,Xue-Wei Liu
RSC Advances Pub Date : 08/12/2014 00:00:00 , DOI:10.1039/C4RA07429G
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