Organic Letters 2007-10-11

Delta-sultone formation through Rh-catalyzed C-H insertion.

Scott A Wolckenhauer, A Sloan Devlin, J Du Bois

Index: Org. Lett. 9(21) , 4363-6, (2007)

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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.