Delta-sultone formation through Rh-catalyzed C-H insertion |
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Authors: | Wolckenhauer Scott A Devlin A Sloan Bois J Du |
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Institution: | Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. |
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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. |
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