Stereoselektive c-glycosidsynthese durch titan-(iv)-katalysierte addition von silylenolethern an 2-acyloxy-3-keto-glycale

Abstract C-Glycosides are stereoselectively formed by the titan-(IV)-catalysed addition of silyl enolethers 2 to 2,4,6-tri-O-acyl-1-deoxy-D-erythro-hex-1-enopyran-3-uloses 1 followed by elimination of the 4-acyloxy substituent. Cyclohexenyl silylether 2a reacts with 2-acetoxy-3-keto-glycal derivative la forming only one product 3a . Thus, the reaction seems to be diastereospecific with respect to both new chiral centers of the product.