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Catalytic asymmetric transannulation of NH-1,2,3-triazoles with olefins.

ABSTRACT: 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.

SUBMITTER: Kwok SW 

PROVIDER: S-EPMC4082713 | biostudies-literature | 2014 Mar

REPOSITORIES: biostudies-literature

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Catalytic asymmetric transannulation of NH-1,2,3-triazoles with olefins.

Kwok Sen Wai SW   Zhang Li L   Grimster Neil P NP   Fokin Valery V VV  

Angewandte Chemie (International ed. in English) 20140301 13

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 rearrangemen  ...[more]

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