Literature DB >> 12816449

Solvent-dependent chemoselectivities in Ce(IV)-mediated oxidative coupling reactions.

Yang Zhang1, Andrew J Raines, Robert A Flowers.   

Abstract

The oxidative coupling of 1,3-diketones, beta-keto esters, and beta-keto silyl enol ethers with allyl trimethylsilane in the presence of CTAN was investigated. In the case of acyclic diketones and esters, different chemoselectivities were observed in CH(3)CN and CH(2)Cl(2) leading to good yields of allylation and dihydrofuran products, respectively. [reaction: see text]

Entities:  

Year:  2003        PMID： 12816449     DOI： 10.1021/ol034763d

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


  7 in total

1.  Mechanisms of Mn(OAc)(3)-based oxidative free-radical additions and cyclizations.

Authors:  Barry B Snider
Journal:  Tetrahedron       Date:  2009-12-26       Impact factor: 2.457

2.  An efficient and general approach to beta-functionalized ketones.

Authors:  Jingliang Jiao; Larry X Nguyen; Dennis R Patterson; Robert A Flowers
Journal:  Org Lett       Date:  2007-03-03       Impact factor: 6.005

3.  Synthesis of gamma-halogenated ketones via the Ce(IV)-mediated oxidative coupling of cyclobutanols and inorganic halides.

Authors:  Brian M Casey; Cynthia A Eakin; Robert A Flowers
Journal:  Tetrahedron Lett       Date:  2009-03-25       Impact factor: 2.415

4.  Facile Route to Tetrasubstituted Pyrazoles Utilizing Ceric Ammonium Nitrate.

Authors:  James J Devery; Pramod K Mohanta; Brian M Casey; Robert A Flowers
Journal:  Synlett       Date:  2009       Impact factor: 2.454

5.  Total synthesis of the lycopodium alkaloid (+)-serratezomine A.

Authors:  Aroop Chandra; Julie A Pigza; Jeong-Seok Han; Daniel Mutnick; Jeffrey N Johnston
Journal:  J Am Chem Soc       Date:  2009-03-18       Impact factor: 15.419

6.  Oxidative carbon-carbon bond formation via allyldimethylsilyl enol ethers.

Authors:  Leah C Konkol; Brian T Jones; Regan J Thomson
Journal:  Org Lett       Date:  2009-12-03       Impact factor: 6.005

7.  Mechanistic studies of Ce(IV)-mediated oxidation of beta-dicarbonyls: solvent-dependent behavior of radical cation intermediates.

Authors:  Jingliang Jiao; Yang Zhang; James J Devery; Luna Xu; Jennifer Deng; Robert A Flowers
Journal:  J Org Chem       Date:  2007-06-28       Impact factor: 4.354
  7 in total

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