Literature DB >> 30907595

Rh(II)-Catalyzed Nitrene-Transfer [5 + 1] Cycloadditions of Aryl-Substituted Vinylcyclopropanes.

Logan A Combee1, Shea L Johnson1, Julie E Laudenschlager1, Michael K Hilinski1.   

Abstract

Formal [5 + 1] cycloadditions between aryl-substituted vinylcyclopropanes and nitrenoid precursors are reported. The method, which employs Rh2(esp)2 as a catalyst, leads to the highly regioselective formation of substituted tetrahydropyridines. Preliminary mechanistic studies support a stepwise, polar mechanism enabled by the previously observed Lewis acidity of Rh-nitrenoids. Overall, this work expands the application of nitrene-transfer cycloaddition, a relatively underexplored approach to heterocycle synthesis, to the formation of six-membered rings.

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Year:  2019        PMID： 30907595      PMCID： PMC6492922          DOI： 10.1021/acs.orglett.9b00594

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  26 in total

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Authors:  B Darses; R Rodrigues; L Neuville; M Mazurais; P Dauban
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2.  Nitrene chemistry in organic synthesis: still in its infancy?

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4.  Direct stereospecific synthesis of unprotected N-H and N-Me aziridines from olefins.

Authors:  Jawahar L Jat; Mahesh P Paudyal; Hongyin Gao; Qing-Long Xu; Muhammed Yousufuddin; Deepa Devarajan; Daniel H Ess; László Kürti; John R Falck
Journal:  Science       Date:  2014-01-03       Impact factor: 47.728

5.  Alkene functionalization for the stereospecific synthesis of substituted aziridines by visible-light photoredox catalysis.

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Journal:  Chem Commun (Camb)       Date:  2018-02-20       Impact factor: 6.222

6.  Total syntheses of (+)-australine and (-)-7-epialexine.

Authors:  W H Pearson; J V Hines
Journal:  J Org Chem       Date:  2000-09-08       Impact factor: 4.354

Review 7.  Applications of Fluorine in Medicinal Chemistry.

Authors:  Eric P Gillis; Kyle J Eastman; Matthew D Hill; David J Donnelly; Nicholas A Meanwell
Journal:  J Med Chem       Date:  2015-07-22       Impact factor: 7.446

8.  Transfer of chirality in the rhodium-catalyzed intramolecular formal hetero-[5 + 2] cycloaddition of vinyl aziridines and alkynes: stereoselective synthesis of fused azepine derivatives.

Authors:  Jian-Jun Feng; Tao-Yan Lin; Hai-Hong Wu; Junliang Zhang
Journal:  J Am Chem Soc       Date:  2015-03-16       Impact factor: 15.419

9.  Catalytic intermolecular alkene oxyamination with nitrenes.

Authors:  Geoffroy Dequirez; Jennifer Ciesielski; Pascal Retailleau; Philippe Dauban
Journal:  Chemistry       Date:  2014-06-17       Impact factor: 5.236

10.  Chirality Transfer in Rhodium(I)-Catalyzed [3 + 2]-Cycloaddition of Vinyl Aziridines and Oxime Ethers: Atom-Economical Synthesis of Chiral Imidazolidines.

Authors:  Tao-Yan Lin; Hai-Hong Wu; Jian-Jun Feng; Junliang Zhang
Journal:  Org Lett       Date:  2018-06-04       Impact factor: 6.005
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  1 in total

1.  Catalytic [5 + 1]-Cycloadditions of Vinylcyclopropanes and Vinylidenes.

Authors:  Conner M Farley; Kohei Sasakura; You-Yun Zhou; Vibha V Kanale; Christopher Uyeda
Journal:  J Am Chem Soc       Date:  2020-02-27       Impact factor: 15.419
  1 in total

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