Literature DB >> 19254039

Oxidation of oximes to nitrile oxides with hypervalent iodine reagents.

Brian A Mendelsohn1, Shelley Lee, Simon Kim, Florian Teyssier, Virender S Aulakh, Marco A Ciufolini.   

Abstract

Iodobenzene diacetate in MeOH containing a catalytic amount of TFA efficiently oxidizes aldoximes to nitrile oxides. The latter may be trapped in situ with olefins in a bimolecular or an intramolecular mode. The new method enables the execution of tandem oxidative dearomatization of phenols/intramolecular nitrile oxide cycloaddition sequences leading to useful synthetic intermediates.

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Year:  2009        PMID： 19254039     DOI： 10.1021/ol900194v

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


  12 in total

1.  Metal-free sequential [3 + 2]-dipolar cycloadditions using cyclooctynes and 1,3-dipoles of different reactivity.

Authors:  Brian C Sanders; Frédéric Friscourt; Petr A Ledin; Ngalle Eric Mbua; Selvanathan Arumugam; Jun Guo; Thomas J Boltje; Vladimir V Popik; Geert-Jan Boons
Journal:  J Am Chem Soc       Date:  2010-12-23       Impact factor: 15.419

Review 2.  Dearomatization strategies in the synthesis of complex natural products.

Authors:  Stéphane P Roche; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-19       Impact factor: 15.336

3.  A hypervalent iodine-induced double annulation enables a concise synthesis of the pentacyclic core structure of the cortistatins.

Authors:  Jessica L Frie; Christopher S Jeffrey; Erik J Sorensen
Journal:  Org Lett       Date:  2009-12-03       Impact factor: 6.005

4.  Synthesis of the spiroiminal moiety and approaches to the synthesis of marineosins A and B.

Authors:  Xiao-Chuan Cai; Barry B Snider
Journal:  J Org Chem       Date:  2013-11-21       Impact factor: 4.354

5.  Multi-Functionalization of Polymers by Strain-Promoted Cycloadditions.

Authors:  Petr A Ledin; Nagesh Kolishetti; Geert-Jan Boons
Journal:  Macromolecules       Date:  2013-10-08       Impact factor: 5.985

Review 6.  The chemical synthesis of tetrodoxin: an ongoing quest.

Authors:  Jaclyn Chau; Marco A Ciufolini
Journal:  Mar Drugs       Date:  2011-10-20       Impact factor: 6.085

7.  Synthesis, Identification, and Structure-Activity Relationship Analysis of GATA4 and NKX2-5 Protein-Protein Interaction Modulators.

Authors:  Mikael Jumppanen; Sini M Kinnunen; Mika J Välimäki; Virpi Talman; Samuli Auno; Tanja Bruun; Gustav Boije Af Gennäs; Henri Xhaard; Ingo B Aumüller; Heikki Ruskoaho; Jari Yli-Kauhaluoma
Journal:  J Med Chem       Date:  2019-09-03       Impact factor: 7.446

8.  [2 + 2 + 1] Cycloaddition of N-tosylhydrazones, tert-butyl nitrite and alkenes: a general and practical access to isoxazolines.

Authors:  Liang Ma; Feng Jin; Xionglve Cheng; Suyan Tao; Gangzhong Jiang; Xingxing Li; Jinwei Yang; Xiaoguang Bao; Xiaobing Wan
Journal:  Chem Sci       Date:  2021-06-22       Impact factor: 9.825

9.  A one-pot synthesis of 3-trifluoromethyl-2-isoxazolines from trifluoromethyl aldoxime.

Authors:  Raoni S B Gonçalves; Michael Dos Santos; Guillaume Bernadat; Danièle Bonnet-Delpon; Benoit Crousse
Journal:  Beilstein J Org Chem       Date:  2013-11-07       Impact factor: 2.883

10.  Mechanochemical Synthesis and Isomerization of N-Substituted Indole-3-carboxaldehyde Oximes †.

Authors:  Matej Baláž; Zuzana Kudličková; Mária Vilková; Ján Imrich; Ľudmila Balážová; Nina Daneu
Journal:  Molecules       Date:  2019-09-14       Impact factor: 4.411
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