Generaton of Thiocarbonyl Ylides from the Rhodium(II) -Catalyzed Cyclization of Diazothiocarbonyl Compounds

Albert Padwa; Frederic R. Kinder; Lin Zhi

doi:10.1055/s-1991-21980

Synlett 1991; 1991(4): 287-288
DOI: 10.1055/s-1991-21980

letter

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Generaton of Thiocarbonyl Ylides from the Rhodium(II) -Catalyzed Cyclization of Diazothiocarbonyl Compounds

Albert Padwa^* , Frederic R. Kinder, Lin Zhi

^*Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA

Abstract

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The rhodium(II)-catalyzed reaction of an α-diazoβ-oxo esters containing a thiocarbonyl group (ethyl 2-diazo-5-(N-methyl-N-phenylthiocarbamoyl)-3-oxopentanoate produced a cyclic thiocarbonyl ylide which extruded sulfur via a transient episulfide intermediate to give ethyl 2-(N-methyl-N-phenylamino)-5-oxo-2-cyclopentene-1-carboxylate. The mesoionic anhydro-4-hydroxythiazolium hydroxide system derived from cyclization of a diazothioamide [methyl 2-diazo-3-oxo-3-(2-thioxo-1-pyrrolidinyl)-propanoate] underwent a 1,3-dipolar cycloaddition in the presence of N-phenylmaleimide to give methyl 4,9a-epithio-2-phenyl-1,3,5-trioxoperhydropyrrole[3,4-g]-indolizine-4-carboxylate.

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