title: Delta-sultone formation through Rh-catalyzed C-H insertion.
abstract: Rhodium-catalyzed reactions of sulfonate ester derivatives are biased strongly toward 1,6-insertion and thus offer a general method for assembling delta-sultones. Two protocols for staging this cyclization reaction are described, which capitalize on the unique ability of either diazo or iodonium ylide intermediates to form Rh-carbene species. The value of these heterocycles for fine chemicals synthesis is demonstrated in both reductive and oxidative reactions that make possible excision of the -SO3- moiety.
authors: Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA.
authors: Scott A
authors: SA
authors: Wolckenhauer
authors: A Sloan
authors: AS
authors: Devlin
authors: J Du
authors: JD
authors: Bois
mesh_terms: D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D004952:Esters; D006571:Heterocyclic Compounds / Q000737:chemistry*; D015394:Molecular Structure; D009282:Naphthalenesulfonates / Q000138:chemical synthesis* / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D004952:Esters; D006571:Heterocyclic Compounds; D009282:Naphthalenesulfonates; C016768:naphthosultone; D012238:Rhodium