Literature DB >> 26176378

P(NMe2)3-Mediated Umpolung Alkylation and Nonylidic Olefination of α-Keto Esters.

Sunewang Rixin Wang1, Alexander T Radosevich1.   

Abstract

A commercial phosphorus-based reagent (P(NMe2)3) mediates umpolung alkylation of methyl aroylformates with benzylic and allylic bromides, leading to either Barbier-type addition or ylide-free olefination products upon workup. The reaction sequence is initiated by a two-electron redox addition of the tricoordinate phosphorus reagent with an α-keto ester compound (Kukhtin-Ramirez addition). A mechanistic rationale is offered for the chemoselectivity upon which the success of this nonmetal mediated C-C bond forming strategy is based.

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Year:  2015        PMID： 26176378      PMCID： PMC4769642          DOI： 10.1021/acs.orglett.5b01784

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


  19 in total

1.  A phosphetane catalyzes deoxygenative condensation of α-keto esters and carboxylic acids via P(III)/P(V)═O redox cycling.

Authors:  Wei Zhao; Patrick K Yan; Alexander T Radosevich
Journal:  J Am Chem Soc       Date:  2015-01-13       Impact factor: 15.419

2.  Synthesis of oxazolidine-2,4-diones by a tandem phosphorus-mediated carboxylative condensation-cyclization reaction using atmospheric carbon dioxide.

Authors:  Wen-Zhen Zhang; Tian Xia; Xu-Tong Yang; Xiao-Bing Lu
Journal:  Chem Commun (Camb)       Date:  2015-04-11       Impact factor: 6.222

3.  Stereoselective synthesis of Z-alpha-aryl-alpha,beta-unsaturated esters.

Authors:  Neelakandha S Mani; Christopher M Mapes; Jiejun Wu; Xiaohu Deng; Todd K Jones
Journal:  J Org Chem       Date:  2006-06-23       Impact factor: 4.354

4.  P(MeNCH2CH2)3N: a highly selective reagent for synthesizing trans-epoxides from aryl aldehydes

Authors: 
Journal:  J Org Chem       Date:  2000-07-28       Impact factor: 4.354

5.  A nonmetal approach to α-heterofunctionalized carbonyl derivatives by formal reductive X-H insertion.

Authors:  Eric J Miller; Wei Zhao; Jonathan D Herr; Alexander T Radosevich
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-20       Impact factor: 15.336

6.  Three component coupling of alpha-iminoesters via umpolung addition of organometals: synthesis of alpha,alpha-disubstituted alpha-amino acids.

Authors:  Joshua S Dickstein; Michael W Fennie; Amber L Norman; Betty J Paulose; Marisa C Kozlowski
Journal:  J Am Chem Soc       Date:  2008-11-26       Impact factor: 15.419

7.  Palladium-catalyzed cross coupling reaction of benzyl bromides with diazoesters for stereoselective synthesis of (E)-alpha,beta-diarylacrylates.

Authors:  Wing-Yiu Yu; Yuk-Tai Tsoi; Zhongyuan Zhou; Albert S C Chan
Journal:  Org Lett       Date:  2009-01-15       Impact factor: 6.005

8.  A C(sp3)-C(sp3) bond forming reductive condensation of α-keto esters and enolizable carbon pronucleophiles.

Authors:  Wei Zhao; Darla M Fink; Carolyn A Labutta; Alexander T Radosevich
Journal:  Org Lett       Date:  2013-06-05       Impact factor: 6.005

9.  Reductive homocondensation of benzylidene- and alkylidenepyruvate esters by a P(NMe2)3-mediated tandem reaction.

Authors:  Sunewang Rixin Wang; Alexander T Radosevich
Journal:  Org Lett       Date:  2013-04-11       Impact factor: 6.005

10.  Tandem N-alkylation-C-allylation reaction of alpha-imino esters with organoaluminums and allyltributyltin.

Authors:  Yasuki Niwa; Makoto Shimizu
Journal:  J Am Chem Soc       Date:  2003-04-02       Impact factor: 15.419
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