Chemoselective ligation of sulfinic acids with aryl-nitroso compounds - PubMed (original) (raw)

Chemoselective ligation of sulfinic acids with aryl-nitroso compounds

Mauro Lo Conte et al. Angew Chem Int Ed Engl. 2012.

Abstract

Making a comeback: The inefficient condensation of sulfinic acid and aryl nitroso compounds has been transformed into a chemoselective process that converts sulfinic acid into stable cyclic sulfonamide analogues (see scheme). This ligation proceeds rapidly under aqueous conditions in high yield, and lays the groundwork for the development of sulfinic acid detection methods in biological systems.

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Figures

Figure 1

Resonance and structures of sulfinate anions in this study. Boc = _tert_-butoxycarbonyl.

Scheme 1

Condensation reaction between a C-nitroso compound and aryl sulfinic acid.

Scheme 2

Proposed mechanism of N-sulfonylbenzisoxazolone formation.

Scheme 3

Control experiments for the ligation of sulfinic acid by 7f in the presence of excess thiols.

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Chemoselective ligation of sulfinic acids with aryl-nitroso compounds - PubMed (original) (raw)