A variety of diazo sulfonylamidines (1) was prepared by the cycloaddition of sulfonyl azides and ynamines. In the presence of chiral rhodium(II) carboxylates, an unexpected intramolecular transfer of an oxygen atom from sulfur to carbon was observed. This formal reduction of sulfur occured rapidly under mild reaction conditions, to obtain enantioenriched sulfinylamidines (2) in excellent yield and with high enantioselectivity.

Intramolecular catalytic asymmetric transformations of diazo sulfonylamidines: An unexpexted formal reduction of sulfur(VI) to sulfur(IV)

243rd National Meeting (2012)

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