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Catalytic Asymmetric Transannulation of NH-1,2,3-Triazoles with Olefins


  • This work was supported by the National Institute of General Medical Sciences, National Institutes of Health (GM087620), and Ministry of Science and Education of Russian Federation (14.A12.31.0005). We thank Prof. Hisashi Yamamoto (Univ. of Chicago) for his kind gift of chiral phosphoric acids.


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 Brønsted acid catalyzed rearrangement of cyclopropylimines into enantioenriched 2,3-dihydropyrroles.