Delta-sultone formation through Rh-catalyzed C-H insertion.
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.
Wolckenhauer
Scott A
SA
Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA.
Devlin
A Sloan
AS
Bois
J Du
JD
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
D004952:Esters; D006571:Heterocyclic Compounds; D009282:Naphthalenesulfonates; C016768:naphthosultone; D012238:Rhodium