Literature DB >> 19946457

A Simple Procedure for C-C Bond Cleavage of Aromatic and Aliphatic Epoxides with Aqueous Sodium Periodate Under Ambient Conditions.

Caitlin M Binder1, Darryl D Dixon, Erik Almaraz, Marcus A Tius, Bakthan Singaram.   

Abstract

The sodium periodate mediated oxidative cleavage of the C-C bond of twelve epoxides is reported with yields of the corresponding carbonyl compounds in up to 91%. This is a two-step reaction that proceeds through a rate-limiting epoxide opening to a vicinal diol that is cleaved in situ to the corresponding carbonyl compound. This method serves as a chemoselective alternative to ozonolysis.

Entities:  

Year:  2008        PMID： 19946457      PMCID： PMC2783163          DOI： 10.1016/j.tetlet.2008.02.142

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  5 in total

1.  A practical and mild method for the highly selective conversion of terminal alkenes into aldehydes through epoxidation-isomerization with ruthenium(IV)-porphyrin catalysts.

Authors:  Jian Chen; Chi-Ming Che
Journal:  Angew Chem Int Ed Engl       Date:  2004-09-20       Impact factor: 15.336

2.  Ruthenium-catalyzed oxidative cleavage of olefins to aldehydes.

Authors:  D Yang; C Zhang
Journal:  J Org Chem       Date:  2001-07-13       Impact factor: 4.354

3.  Activated iodosylbenzene monomer as an ozone equivalent: oxidative cleavage of carbon-carbon double bonds in the presence of water.

Authors:  Kazunori Miyamoto; Norihiro Tada; Masahito Ochiai
Journal:  J Am Chem Soc       Date:  2007-02-20       Impact factor: 15.419

4.  A diosphenol-based strategy for the total synthesis of (-)-terpestacin.

Authors:  Barry M Trost; Guangbin Dong; Jennifer A Vance
Journal:  J Am Chem Soc       Date:  2007-03-08       Impact factor: 15.419

5.  Development and application of versatile bis-hydroxamic acids for catalytic asymmetric oxidation.

Authors:  Allan U Barlan; Wei Zhang; Hisashi Yamamoto
Journal:  Tetrahedron       Date:  2007-07-02       Impact factor: 2.457
  5 in total
  4 in total

1.  A formal synthesis of the C1-C9 fragment of amphidinolide C employing the Tamaru reaction.

Authors:  Mahesh P Paudyal; Nigam P Rath; Christopher D Spilling
Journal:  Org Lett       Date:  2010-07-02       Impact factor: 6.005

2.  An expedient procedure for the oxidative cleavage of olefinic bonds with PhI(OAc)2, NMO, and catalytic OsO4.

Authors:  K C Nicolaou; Vikrant A Adsool; Christopher R H Hale
Journal:  Org Lett       Date:  2010-04-02       Impact factor: 6.005

Review 3.  Structural derivatization strategies of natural phenols by semi-synthesis and total-synthesis.

Authors:  Ding Lin; Senze Jiang; Ailian Zhang; Tong Wu; Yongchang Qian; Qingsong Shao
Journal:  Nat Prod Bioprospect       Date:  2022-03-07

4.  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
  4 in total

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