Literature DB >> 23738614

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

Wei Zhao1, Darla M Fink, Carolyn A Labutta, Alexander T Radosevich.   

Abstract

The preparation of densely functionalized unsymmetrical 1,4-dicarbonyl structural motifs by a phosphorus(III)-mediated reductive condensation of α-keto esters and enolizable carbon pronucleophiles is described. The reaction, which is initiated by Kukhtin-Ramirez addition of commercially available tris(dimethylamino)phosphine to the α-keto ester substrate, proceeds rapidly under mild conditions.

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Year:  2013        PMID: 23738614     DOI: 10.1021/ol401276b

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


  4 in total

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

Authors:  Sunewang Rixin Wang; Alexander T Radosevich
Journal:  Org Lett       Date:  2015-07-15       Impact factor: 6.005

Review 2.  Phosphine Organocatalysis.

Authors:  Hongchao Guo; Yi Chiao Fan; Zhanhu Sun; Yang Wu; Ohyun Kwon
Journal:  Chem Rev       Date:  2018-09-27       Impact factor: 60.622

3.  Phosphorus(III)-Mediated Reductive Condensation of α-Keto Esters and Protic Pronucleophiles.

Authors:  Wei Zhao; Alexander T Radosevich
Journal:  Organic Synth       Date:  2015

4.  Main Group Redox Catalysis of Organopnictogens: Vertical Periodic Trends and Emerging Opportunities in Group 15.

Authors:  Jeffrey M Lipshultz; Gen Li; Alexander T Radosevich
Journal:  J Am Chem Soc       Date:  2021-01-19       Impact factor: 15.419

  4 in total

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