Literature DB >> 19489638

Cyclocarboamination of alkynes with aziridines: synthesis of 2,3-dihydropyrroles by a catalyzed formal [3 + 2] cycloaddition.

Paul A Wender1, Daniel Strand.   

Abstract

An efficient cyclocarboamination reaction of nonactivated alkynes with aziridines, catalyzed by Lewis or Bronsted acids, to form 2,3-dihydropyrroles through a formal [3+2] cycloaddition, is described. The reaction provides a wide range of polysubstituted dihydropyrroles in a highly regioselective manner, is scalable, proceeds under mild reaction conditions, and uses low catalyst loadings.

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Year:  2009        PMID: 19489638     DOI: 10.1021/ja901799s

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  7 in total

1.  Asymmetric Radical Bicyclization of Allyl Azidoformates via Cobalt(II)-Based Metalloradical Catalysis.

Authors:  Huiling Jiang; Kai Lang; Hongjian Lu; Lukasz Wojtas; X Peter Zhang
Journal:  J Am Chem Soc       Date:  2017-06-29       Impact factor: 15.419

2.  Intramolecular Radical Aziridination of Allylic Sulfamoyl Azides by Cobalt(II)-Based Metalloradical Catalysis: Effective Construction of Strained Heterobicyclic Structures.

Authors:  Huiling Jiang; Kai Lang; Hongjian Lu; Lukasz Wojtas; X Peter Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2016-08-11       Impact factor: 15.336

3.  Intramolecular ring-opening from a CO2-derived nucleophile as the origin of selectivity for 5-substituted oxazolidinone from the (salen)Cr-catalyzed [aziridine + CO2] coupling.

Authors:  Debashis Adhikari; Aaron W Miller; Mu-Hyun Baik; SonBinh T Nguyen
Journal:  Chem Sci       Date:  2014-11-21       Impact factor: 9.825

4.  Asymmetric [3 + 2] cycloaddition of donor-acceptor aziridines with aldehydes via carbon-carbon bond cleavage.

Authors:  Yuting Liao; Xiaohua Liu; Yu Zhang; Yali Xu; Yong Xia; Lili Lin; Xiaoming Feng
Journal:  Chem Sci       Date:  2016-02-23       Impact factor: 9.825

5.  Phosphine-Promoted [4 + 3] Annulation of Allenoate with Aziridines for Synthesis of Tetrahydroazepines: Phosphine-Dependent [3 + 3] and [4 + 3] Pathways.

Authors:  Honglei Liu; Yan Lin; Yan Zhao; Miaoren Xiao; Leijie Zhou; Qijun Wang; Cheng Zhang; Dongqi Wang; Ohyun Kwon; Hongchao Guo
Journal:  RSC Adv       Date:  2019-01-09       Impact factor: 4.036

Review 6.  Metal-mediated synthesis of pyrrolines.

Authors:  Noelia S Medran; Agustina La-Venia; Sebastian A Testero
Journal:  RSC Adv       Date:  2019-02-27       Impact factor: 4.036

7.  Synthesis of cis-C-iodo-N-tosyl-aziridines using diiodomethyllithium: reaction optimization, product scope and stability, and a protocol for selection of stationary phase for chromatography.

Authors:  Tom Boultwood; Dominic P Affron; Aaron D Trowbridge; James A Bull
Journal:  J Org Chem       Date:  2013-06-18       Impact factor: 4.354

  7 in total

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