Literature DB >> 18710285

Cobalt-catalyzed asymmetric olefin aziridination with diphenylphosphoryl azide.

Jess E Jones1, Joshua V Ruppel, Guang-Yao Gao, Thomas M Moore, X Peter Zhang.   

Abstract

The cobalt(II) complexes of D2-symmetric chiral porphyrins, such as 3,5-Di(t)Bu-ChenPhyrin P5, can catalyze asymmetric olefin aziridination with diphenylphosphoryl azide (DPPA) as a nitrene source. Acceptable asymmetric inductions were observed for the [Co(P5)]-based catalytic system, forming the desired N-phosphorus-substituted aziridines in moderate to high yields and good enantioselectivities.

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Year:  2008        PMID： 18710285     DOI： 10.1021/jo801151x

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  17 in total

1.  Characterization of Porphyrin-Co(III)-'Nitrene Radical' Species Relevant in Catalytic Nitrene Transfer Reactions.

Authors:  Monalisa Goswami; Volodymyr Lyaskovskyy; Sérgio R Domingos; Wybren Jan Buma; Sander Woutersen; Oliver Troeppner; Ivana Ivanović-Burmazović; Hongjian Lu; Xin Cui; X Peter Zhang; Edward J Reijerse; Serena DeBeer; Matti M van Schooneveld; Florian Felix Pfaff; Kallol Ray; Bas de Bruin
Journal:  J Am Chem Soc       Date:  2015-04-16       Impact factor: 15.419

2.  Elucidation of the Reaction Mechanism of C2 + N1 Aziridination from Tetracarbene Iron Catalysts.

Authors:  Sara B Isbill; Preeti P Chandrachud; Jesse L Kern; David M Jenkins; Sharani Roy
Journal:  ACS Catal       Date:  2019-05-31       Impact factor: 13.084

3.  Characterization of Tunable Radical Metal-Carbenes: Key Intermediates in Catalytic Cyclopropanation.

Authors:  Jonathan L Belof; Christian R Cioce; Xue Xu; X Peter Zhang; Brian Space; H Lee Woodcock
Journal:  Organometallics       Date:  2011-04-29       Impact factor: 3.876

4.  Recent advances in transition metal-catalyzed N-atom transfer reactions of azides.

Authors:  Tom G Driver
Journal:  Org Biomol Chem       Date:  2010-07-08       Impact factor: 3.876

5.  Room Temperature Activation of Aryloxysulfonyl Azides by [Co(II)(TPP)] for Selective Radical Aziridination of Alkenes via Metalloradical Catalysis.

Authors:  Velusamy Subbarayan; Li-Mei Jin; Cui Xin; X Peter Zhang
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

6.  Rh2(II)-catalyzed intramolecular aliphatic C-H bond amination reactions using aryl azides as the N-atom source.

Authors:  Quyen Nguyen; Ke Sun; Tom G Driver
Journal:  J Am Chem Soc       Date:  2012-04-24       Impact factor: 15.419

7.  Synthesis of amide isosteres of schweinfurthin-based stilbenes.

Authors:  David P Stockdale; John A Beutler; David F Wiemer
Journal:  Bioorg Med Chem       Date:  2017-08-09       Impact factor: 3.641

8.  Effective synthesis of chiral N-fluoroaryl aziridines through enantioselective aziridination of alkenes with fluoroaryl azides.

Authors:  Li-Mei Jin; Xue Xu; Hongjian Lu; Xin Cui; Lukasz Wojtas; X Peter Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2013-04-15       Impact factor: 15.336

9.  Exceptional selectivity in cyclopropanation reactions catalyzed by chiral cobalt(II)-porphyrin catalysts.

Authors:  Michael P Doyle
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

10.  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
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