title: Synthesis of differentially substituted 1,2-diamines through advances in C-H amination technology.
abstract: A general, high yielding method for the synthesis of 1,2-diamine derivatives is described that capitalizes on selective, rhodium-catalyzed C-H insertion of hydroxylamine-based sulfamate esters. The resulting Troc-protected oxathiadiazinane heterocycles are easily modified and can be reduced under the mild action of NaI to afford differentially substituted diamine products. This technology offers a number of salient improvements over related C-H and π-bond amination tactics for diamine synthesis.
authors.affiliation: Department of Chemistry, Stanford University, Stanford, California 94305-5080, United States.
authors.forename: David E
authors.initials: DE
authors.lastname: Olson
authors.forename: D Allen
authors.initials: DA
authors.lastname: Roberts
authors.forename: J
authors.initials: J
authors.lastname: Du Bois
mesh_terms: D000586:Amination; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003959:Diamines / Q000138:chemical synthesis* / Q000737:chemistry; D019811:Hydroxylamine / Q000737:chemistry; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D003959:Diamines; D019811:Hydroxylamine; D012238:Rhodium