Literature DB >> 19552390

Cyclization reactions through DDQ-mediated vinyl oxazolidinone oxidation.

Lei Liu1, Paul E Floreancig.   

Abstract

Vinyl oxazolidinones react with DDQ to form alpha,beta-unsaturated acyliminium ions in a new method for forming electrophiles under oxidative conditions. Appended nucleophiles undergo 1,4-addition reactions with these intermediates to form cyclic vinyl oxazolidinones with good levels of diastereocontrol, highlighting a new approach to utilizing oxidative carbon-hydrogen bond functionalization to increase molecular complexity.

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Year:  2009        PMID： 19552390      PMCID： PMC2722373          DOI： 10.1021/ol901188q

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


  28 in total

1.  A stereoselective intramolecular halo-etherification of chiral enamides in the synthesis of halogenated cyclic ethers.

Authors:  Changhong Ko; Richard P Hsung; Ziyad F Al-Rashid; John B Feltenberger; Ting Lu; Jin-Haek Yang; Yonggang Wei; Craig A Zificsak
Journal:  Org Lett       Date:  2007-10-02       Impact factor: 6.005

2.  Functionalizing glycine derivatives by direct C-C bond formation.

Authors:  Liang Zhao; Chao-Jun Li
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

3.  DDQ-mediated direct cross-dehydrogenative-coupling (CDC) between benzyl ethers and simple ketones.

Authors:  Yuhua Zhang; Chao-Jun Li
Journal:  J Am Chem Soc       Date:  2006-04-05       Impact factor: 15.419

4.  Stereochemistry of nucleophilic substitution reactions depending upon substituent: evidence for electrostatic stabilization of pseudoaxial conformers of oxocarbenium ions by heteroatom substituents.

Authors:  Leticia Ayala; Claudia G Lucero; Jan Antoinette C Romero; Sarah A Tabacco; K A Woerpel
Journal:  J Am Chem Soc       Date:  2003-12-17       Impact factor: 15.419

5.  Copper-catalyzed coupling of amides and carbamates with vinyl halides.

Authors:  Lei Jiang; Gabriel E Job; Artis Klapars; Stephen L Buchwald
Journal:  Org Lett       Date:  2003-10-02       Impact factor: 6.005

6.  Structure-reactivity relationships in oxidative carbon-carbon bond forming reactions: a mild and efficient approach to stereoselective syntheses of 2,6-disubstituted tetrahydropyrones.

Authors:  Lijun Wang; John R Seiders; Paul E Floreancig
Journal:  J Am Chem Soc       Date:  2004-10-06       Impact factor: 15.419

7.  Oxidative carbocation formation in macrocycles: synthesis of the neopeltolide macrocycle.

Authors:  Wangyang Tu; Paul E Floreancig
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

8.  Enamide synthesis by copper-catalyzed cross-coupling of amides and potassium alkenyltrifluoroborate salts.

Authors:  Yuri Bolshan; Robert A Batey
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

9.  Cross-dehydrogenative coupling (CDC): exploring C-C bond formations beyond functional group transformations.

Authors:  Chao-Jun Li
Journal:  Acc Chem Res       Date:  2009-02-17       Impact factor: 22.384

10.  CuI/N,N-dimethylglycine-catalyzed coupling of vinyl halides with amides or carbamates.

Authors:  Xianhua Pan; Qian Cai; Dawei Ma
Journal:  Org Lett       Date:  2004-05-27       Impact factor: 6.005
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  16 in total

1.  Synthesis of sulfur-containing heterocycles through oxidative carbon-hydrogen bond functionalization.

Authors:  Yubo Cui; Paul E Floreancig
Journal:  Org Lett       Date:  2012-03-15       Impact factor: 6.005

2.  Stereoselective synthesis of tertiary ethers through geometric control of highly substituted oxocarbenium ions.

Authors:  Lei Liu; Paul E Floreancig
Journal:  Angew Chem Int Ed Engl       Date:  2010-08-09       Impact factor: 15.336

3.  2,3-Dichloro-5,6-dicyano-1,4-benzoquinone-catalyzed reactions employing MnO2 as a stoichiometric oxidant.

Authors:  Lei Liu; Paul E Floreancig
Journal:  Org Lett       Date:  2010-10-15       Impact factor: 6.005

4.  Aromatic cations from oxidative carbon-hydrogen bond cleavage in bimolecular carbon-carbon bond forming reactions.

Authors:  Dane J Clausen; Paul E Floreancig
Journal:  J Org Chem       Date:  2012-07-16       Impact factor: 4.354

5.  Synthesis of bridged inside-outside bicyclic ethers through oxidative transannular cyclization reactions.

Authors:  Xun Han; Paul E Floreancig
Journal:  Org Lett       Date:  2012-07-11       Impact factor: 6.005

6.  Structurally and stereochemically diverse tetrahydropyran synthesis through oxidative C-H bond activation.

Authors:  Lei Liu; Paul E Floreancig
Journal:  Angew Chem Int Ed Engl       Date:  2010-04-12       Impact factor: 15.336

7.  Cyclopropane compatibility with oxidative carbocation formation: total synthesis of clavosolide A.

Authors:  GuangRong Peh; Paul E Floreancig
Journal:  Org Lett       Date:  2012-10-24       Impact factor: 6.005

8.  Bimolecular Coupling Reactions through Oxidatively Generated Aromatic Cations: Scope and Stereocontrol.

Authors:  Yubo Cui; Louis A Villafane; Dane J Clausen; Paul E Floreancig
Journal:  Tetrahedron       Date:  2013-09-09       Impact factor: 2.457

9.  Spiroacetal formation through telescoped cycloaddition and carbon-hydrogen bond functionalization: total synthesis of bistramide A.

Authors:  Xun Han; Paul E Floreancig
Journal:  Angew Chem Int Ed Engl       Date:  2014-09-04       Impact factor: 15.336

Review 10.  Quinone-Catalyzed Selective Oxidation of Organic Molecules.

Authors:  Alison E Wendlandt; Shannon S Stahl
Journal:  Angew Chem Int Ed Engl       Date:  2015-11-04       Impact factor: 15.336
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