Stereoselective construction of anti- and syn-1,2-diol structures via decarbonylative radical coupling of α-alkoxyacyl tellurides

alpha-Alkoxyacyl tellurides derived from D-tartaric acid were utilized for stereoselective coupling reactions with electron-deficient double bonds. Treatment of the alpha-alkoxyacyl tellurides with Et3B/O-2 or Et3B/O-2/HSi(SiMe3)(3) at room temperature promoted acyl radical formation and subsequent decarbonylation to form the corresponding alpha-alkoxy radicals, which added to various C=C and C=N bonds conjugated with electron withdrawing groups. The stereochemical outcomes were defined by the protective groups of the tartrate derivatives: the acetonide and the 2,3-dimethoxybutane-2,3-dioxy acetal controlled the anti and syn-stereoselectivities, respectively. (C) 2016 Elsevier Ltd. All rights reserved.