Catalytic Asymmetric Transannulation of NH‐1, 2, 3‐Triazoles with Olefins1. Issue 13 (14th February 2014)

• Record Type: Journal Article
• Authors: Kwok, Sen Wai; Zhang, Li; Grimster, Neil P.; Fokin, Valery V.
• Is Part Of: Angewandte Chemie international edition. Volume 53:Issue 13(2014)
• Page Start: 3452
• Page End: 3456
• Publication Date: 2014-02-14
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201306706
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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.</p> </abstract>