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Catalytic Asymmetric Transannulation of N H ‐1,2,3‐Triazoles with Olefins
Author(s) -
Kwok Sen Wai,
Zhang Li,
Grimster Neil P.,
Fokin Valery V.
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201306706
Subject(s) - catalysis , carbene , chemistry , brønsted–lowry acid–base theory , combinatorial chemistry , enantioselective synthesis , organic chemistry , stereochemistry
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.