Literature DB >> 20192259

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

K C Nicolaou1, Vikrant A Adsool, Christopher R H Hale.   

Abstract

PhI(OAc)(2) in the presence of OsO(4) (cat.) and 2,6-lutidine cleaves olefinic bonds to yield the corresponding carbonyl compounds, albeit, in some cases, with alpha-hydroxy ketones as byproduct. A more practical and clean protocol to effect oxidative cleavage of olefinic bonds involves NMO, OsO(4) (cat.), 2,6-lutidine, and PhI(OAc)(2).

Entities:  

Mesh：

Substances：

Year:  2010        PMID： 20192259      PMCID： PMC2848477          DOI： 10.1021/ol100290a

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


  9 in total

1.  Reductive Amination of Aldehydes and Ketones with Sodium Triacetoxyborohydride. Studies on Direct and Indirect Reductive Amination Procedures(1).

Authors:  Ahmed F. Abdel-Magid; Kenneth G. Carson; Bruce D. Harris; Cynthia A. Maryanoff; Rekha D. Shah
Journal:  J Org Chem       Date:  1996-05-31       Impact factor: 4.354

2.  A "Green" route to adipic acid: direct oxidation of cyclohexenes with 30 percent hydrogen peroxide

Authors: 
Journal:  Science       Date:  1998-09-11       Impact factor: 47.728

3.  Efficient Oxidative Cleavage of Olefins to Carboxylic Acids with Hydrogen Peroxide Catalyzed by Methyltrioctylammonium Tetrakis(oxodiperoxotungsto)phosphate(3-) under Two-Phase Conditions. Synthetic Aspects and Investigation of the Reaction Course.

Authors:  Ermanno Antonelli; Rino D'Aloisio; Mario Gambaro; Tiziana Fiorani; Carlo Venturello
Journal:  J Org Chem       Date:  1998-10-16       Impact factor: 4.354

4.  Osmium tetroxide-promoted catalytic oxidative cleavage of olefins: an organometallic ozonolysis.

Authors:  Benjamin R Travis; Radha S Narayan; Babak Borhan
Journal:  J Am Chem Soc       Date:  2002-04-17       Impact factor: 15.419

5.  An efficient one-pot approach to bridged bicyclic ring-systems through consecutive hetero-domino transformations: a mechanistic rationale and further rearrangements.

Authors:  Laure Finet; José I Candela Lena; Talbi Kaoudi; Nicolas Birlirakis; Siméon Arseniyadis
Journal:  Chemistry       Date:  2003-08-18       Impact factor: 5.236

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

Authors:  Caitlin M Binder; Darryl D Dixon; Erik Almaraz; Marcus A Tius; Bakthan Singaram
Journal:  Tetrahedron Lett       Date:  2008-04-21       Impact factor: 2.415

7.  Improved procedure for the oxidative cleavage of olefins by OsO4-NaIO4.

Authors:  Wensheng Yu; Yan Mei; Ying Kang; Zhengmao Hua; Zhendong Jin
Journal:  Org Lett       Date:  2004-09-16       Impact factor: 6.005

8.  Concise synthesis of iminocyclitols via Petasis-type aminocyclization.

Authors:  Zhangyong Hong; Lei Liu; Masakazu Sugiyama; Yu Fu; Chi-Huey Wong
Journal:  J Am Chem Soc       Date:  2009-06-24       Impact factor: 15.419

9.  Iodomesitylene-catalyzed oxidative cleavage of carbon-carbon double and triple bonds using m-chloroperbenzoic acid as a terminal oxidant.

Authors:  Kazunori Miyamoto; Yoshihisa Sei; Kentaro Yamaguchi; Masahito Ochiai
Journal:  J Am Chem Soc       Date:  2009-02-04       Impact factor: 15.419
  9 in total
  13 in total

1.  Synthesis and structure-activity relationships of EGCG analogues, a recently identified Hsp90 inhibitor.

Authors:  Anuj Khandelwal; Jessica A Hall; Brian S J Blagg
Journal:  J Org Chem       Date:  2013-08-01       Impact factor: 4.354

2.  Synthesis of (2R,8' S,3' E)-δ-tocodienol, a tocoflexol family member designed to have a superior pharmacokinetic profile compared to δ-tocotrienol.

Authors:  Xingui Liu; Satheesh Gujarathi; Xuan Zhang; Lijian Shao; Marjan Boerma; Cesar M Compadre; Peter A Crooks; Martin Hauer-Jensen; Daohong Zhou; Guangrong Zheng
Journal:  Tetrahedron       Date:  2016-05-12       Impact factor: 2.457

3.  Enantioselective total synthesis and structural assignment of callyspongiolide.

Authors:  Arun K Ghosh; Luke A Kassekert; Joseph D Bungard
Journal:  Org Biomol Chem       Date:  2016-12-07       Impact factor: 3.876

4.  Nature Inspired Molecular Design: Stereoselective Synthesis of Bicyclic and Polycyclic Ethers for Potent HIV-1 Protease Inhibitors.

Authors:  Arun K Ghosh; Margherita Brindisi
Journal:  Asian J Org Chem       Date:  2018-06-08       Impact factor: 3.319

5.  Total synthesis, relay synthesis, and structural confirmation of the C18-norditerpenoid alkaloid neofinaconitine.

Authors:  Yuan Shi; Jeremy T Wilmot; Lars Ulrik Nordstrøm; Derek S Tan; David Y Gin
Journal:  J Am Chem Soc       Date:  2013-09-16       Impact factor: 15.419

6.  Design of Novel Aminoglycoside Derivatives with Enhanced Suppression of Diseases-Causing Nonsense Mutations.

Authors:  Narayana Murthy Sabbavarapu; Michal Shavit; Yarden Degani; Boris Smolkin; Valery Belakhov; Timor Baasov
Journal:  ACS Med Chem Lett       Date:  2016-02-08       Impact factor: 4.345

7.  Enantioselective Synthesis of Both Epimers at C-21 in the Proposed Structure of Cytotoxic Macrolide Callyspongiolide.

Authors:  Arun K Ghosh; Luke A Kassekert
Journal:  Org Lett       Date:  2016-06-22       Impact factor: 6.005

8.  Ring expansion of cyclic 1,2-diols to form medium sized rings via ruthenium catalyzed transfer hydrogenative [4+2] cycloaddition.

Authors:  Zachary A Kasun; Laina M Geary; Michael J Krische
Journal:  Chem Commun (Camb)       Date:  2014-07-18       Impact factor: 6.222

9.  Enantioselective Total Synthesis of (+)-Amphirionin-4.

Authors:  Arun K Ghosh; Prasanth R Nyalapatla
Journal:  Org Lett       Date:  2016-04-26       Impact factor: 6.005

10.  Total syntheses of both enantiomers of amphirionin 4: A chemoenzymatic based strategy for functionalized tetrahydrofurans.

Authors:  Arun K Ghosh; Prasanth R Nyalapatla
Journal:  Tetrahedron       Date:  2017-02-17       Impact factor: 2.457
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.