Literature DB >> 22512349

Pyridine is an organocatalyst for the reductive ozonolysis of alkenes.

Rachel Willand-Charnley1, Thomas J Fisher, Bradley M Johnson, Patrick H Dussault.   

Abstract

Whereas the cleavage of alkenes by ozone typically generates peroxide intermediates that must be decomposed in an accompanying step, ozonolysis in the presence of pyridine directly generates ketones or aldehydes through a process that neither consumes pyridine nor generates any detectable peroxides. The reaction is hypothesized to involve nucleophile-promoted fragmentation of carbonyl oxides via formation of zwitterionic peroxyacetals.

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Year:  2012        PMID: 22512349      PMCID: PMC3365558          DOI: 10.1021/ol300617r

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


  10 in total

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Review 2.  Ozonolysis applications in drug synthesis.

Authors:  Scott G Van Ornum; Robin M Champeau; Richard Pariza
Journal:  Chem Rev       Date:  2006-07       Impact factor: 60.622

3.  Ozonolysis in solvent/water mixtures: direct conversion of alkenes to aldehydes and ketones.

Authors:  Charles E Schiaffo; Patrick H Dussault
Journal:  J Org Chem       Date:  2008-05-28       Impact factor: 4.354

4.  Flow ozonolysis using a semipermeable Teflon AF-2400 membrane to effect gas-liquid contact.

Authors:  Matthew O'Brien; Ian R Baxendale; Steven V Ley
Journal:  Org Lett       Date:  2010-04-02       Impact factor: 6.005

5.  Continuous flow ozonolysis in a laboratory scale reactor.

Authors:  Muhammad Irfan; Toma N Glasnov; C Oliver Kappe
Journal:  Org Lett       Date:  2011-01-26       Impact factor: 6.005

6.  Detection of sterol hydroperoxides on thin-layer chromatoplates by means of the Wurster dyes.

Authors:  L L Smith; F L Hill
Journal:  J Chromatogr       Date:  1972-03-22

7.  Fragmentation of carbonyl oxides by N-oxides: an improved approach to alkene ozonolysis.

Authors:  Chris Schwartz; Joseph Raible; Kyle Mott; Patrick H Dussault
Journal:  Org Lett       Date:  2006-07-20       Impact factor: 6.005

8.  Development of aliphatic alcohols as nucleophiles for palladium-catalyzed DYKAT reactions: total synthesis of (+)-hippospongic acid A.

Authors:  Barry M Trost; Michelle R Machacek; Hong C Tsui
Journal:  J Am Chem Soc       Date:  2005-05-18       Impact factor: 15.419

9.  Ozonolysis of unsaturated organotrifluoroborates.

Authors:  Gary A Molander; David J Cooper
Journal:  J Org Chem       Date:  2007-04-05       Impact factor: 4.354

10.  Complete ozonolysis of alkyl substituted ethenes at -60 degrees C: distributions of ozonide and oligomeric products.

Authors:  Matthew Barton; John R Ebdon; Andrew B Foster; Steve Rimmer
Journal:  Org Biomol Chem       Date:  2005-03-07       Impact factor: 3.876

  10 in total
  8 in total

1.  Rh(III)-Catalyzed C-H Bond Addition/Amine-Mediated Cyclization of Bis-Michael Acceptors.

Authors:  Tyler J Potter; Jonathan A Ellman
Journal:  Org Lett       Date:  2016-07-20       Impact factor: 6.005

2.  An enantioselective enzymatic desymmetrization route to hexahydro-4H-furopyranol, a high-affinity ligand for HIV-1 protease inhibitors.

Authors:  Arun K Ghosh; Anindya Sarkar
Journal:  Tetrahedron Lett       Date:  2017-07-03       Impact factor: 2.415

3.  Total Synthesis and Stereochemical Assignment of Streptide.

Authors:  Nicholas A Isley; Yusuke Endo; Zhi-Chen Wu; Brett C Covington; Leah B Bushin; Mohammad R Seyedsayamdost; Dale L Boger
Journal:  J Am Chem Soc       Date:  2019-10-17       Impact factor: 15.419

4.  Tandem application of C-C bond-forming reactions with reductive ozonolysis.

Authors:  Rachel Willand-Charnley; Patrick H Dussault
Journal:  J Org Chem       Date:  2012-10-02       Impact factor: 4.354

5.  Enantioselective Synthesis of Vicinal All-Carbon Quaternary Centers via Iridium-Catalyzed Allylic Alkylation.

Authors:  J Caleb Hethcox; Samantha E Shockley; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2018-06-11       Impact factor: 15.336

6.  Large-Scale Synthesis of Crystalline 1,2,3,4,6,7-Hexa-O-acetyl-l-glycero-α-d-manno-heptopyranose.

Authors:  Christian Stanetty; Ian R Baxendale
Journal:  European J Org Chem       Date:  2015-03-10

7.  Sensitive detection of ozone by a practical resorufin-based spectroscopic probe with extremely low background signal.

Authors:  Yangyang Zhang; Wen Shi; Xiaohua Li; Huimin Ma
Journal:  Sci Rep       Date:  2013-10-03       Impact factor: 4.379

8.  Oxidative Cleavage of Alkene C=C Bonds Using a Manganese Catalyzed Oxidation with H2O2 Combined with Periodate Oxidation.

Authors:  Francesco Mecozzi; Jia Jia Dong; Davide Angelone; Wesley R Browne; Niek N H M Eisink
Journal:  European J Org Chem       Date:  2019-10-31
  8 in total

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