Ru-Diphosphine catalyzed asymmetric hydrogenation of unprotected β-C-glycosidic ketones

Abstract

Stereoselective reduction of β-C-glycosidic ketones is an effective method for the synthesis of carbohydrate derivatives. We herein report that β-C-glycosidic ketones, not generally considered as functionalized ketones, are unexpectedly hydrogenated by Ru-diphosphine catalysts with excellent stereoselectivity (up to >99 : 1 dr). Further investigation into the effect of the chiral hydroxyl groups during the reaction has also been conducted. This reaction has been performed on a multi-gram scale, providing a novel approach for the construction of chiral centers in carbohydrate derivatives.