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A convenient one-pot asymmetric synthesis of 2,3-dihydropyrroles from in situ generated triflated triazoles and olefins is described that further expands the utility of azavinyl carbene chemistry and provides access to an important class of cyclic enamides. Mechanistic investigations support the involvement of triflated cyclopropylaldimine intermediates in the formation of 2,3-dihydropyrrole. To the best of our knowledge, this is the first example of a chiral Bronsted acid catalyzed rearrangement of cyclopropylimines into enantioenriched 2,3-dihydropyrroles.

A new tandem catalysis strategy is developed, that transforms alkyne derivatives into (E)-enol equivalents.

Highly reactive rhodium(II) N-trifluoromethylsulfonyl azavinyl carbenes are formed in situ from NH-1,2,3-triazoles, triflic anhydride, and rhodium carboxylates. They rapidly and selectively react with olefins, providing cyclopropane carboxaldehydes and 2,3-dihydropyrroles in generally excellent yields and high enantio- and diastereoselectivity.