Catalytic C-H amination for the preparation of substituted 1,2-diamines.
Rhodium-catalyzed C-H insertion of hydroxylamine-derived sulfamate esters makes possible the synthesis of unique oxathiadiazinane heterocycles, which upon mild reduction furnish differentially substituted 1,2-diamine products. This highly chemo- and diastereoselective transformation underscores the power of catalytic C-H functionalization as a general approach to C-N bond construction.
Olson
David E
DE
Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA.
Du Bois
J
J
D000586:Amination; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D003959:Diamines / Q000138:chemical synthesis*; D004952:Esters / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry; D019811:Hydroxylamine / Q000737:chemistry*; D008956:Models, Chemical; D009584:Nitrogen / Q000737:chemistry; D010084:Oxidation-Reduction; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*
D003959:Diamines; D004952:Esters; D013449:Sulfonamides; D019811:Hydroxylamine; D002244:Carbon; D006859:Hydrogen; D012238:Rhodium; D009584:Nitrogen