Literature DB >> 34267406

Phosphite-Mediated Reductive Cross-Coupling of Isatins and Nitrostyrenes.

Somayeh Motevalli1, Jeffrey S Johnson1.   

Abstract

A new reductive coupling reaction between N-alkylisatins, dimethyl phosphite, and nitrostyrenes has been developed. The reaction relies on Pudovik addition, subsequent phosphonate-phosphate rearrangement, and Michael-type addition of a transient carbanion on the indolinone with β-nitrostyrenes. This protocol introduces a convenient and versatile method for the construction of polyfunctionalized tertiary phosphates under mild conditions. Chiral general bases catalyze the title reaction with promising levels of enantioselectivity.

Entities:  

Keywords:  Michael addition; nucleophilic addition; phosphates; rearrangement; reduction

Year:  2017        PMID： 34267406      PMCID： PMC8278291          DOI： 10.1055/s-0036-1588170

Source DB:  PubMed          Journal:  Synthesis (Stuttg)        ISSN： 0039-7881            Impact factor:   3.157


  28 in total

1.  Catalytic enantioselective construction of quaternary stereocenters by direct vinylogous Michael addition of deconjugated butenolides to nitroolefins.

Authors:  Madhu Sudan Manna; Vikas Kumar; Santanu Mukherjee
Journal:  Chem Commun (Camb)       Date:  2012-04-18       Impact factor: 6.222

2.  Highly enantioselective conjugate addition of nitromethane to chalcones using bifunctional cinchona organocatalysts.

Authors:  Benedek Vakulya; Szilárd Varga; Antal Csámpai; Tibor Soós
Journal:  Org Lett       Date:  2005-05-12       Impact factor: 6.005

3.  Highly enantioselective Michael addition of nitroalkanes to chalcones using chiral squaramides as hydrogen bonding organocatalysts.

Authors:  Wen Yang; Da-Ming Du
Journal:  Org Lett       Date:  2010-11-05       Impact factor: 6.005

4.  Highly enantioselective direct alkylation of arylacetic acids with chiral lithium amides as traceless auxiliaries.

Authors:  Craig E Stivala; Armen Zakarian
Journal:  J Am Chem Soc       Date:  2011-07-15       Impact factor: 15.419

5.  Stereochemical surprises in the Lewis acid-mediated allylation of isatins.

Authors:  Devendra J Vyas; Roland Fröhlich; Martin Oestreich
Journal:  J Org Chem       Date:  2010-10-01       Impact factor: 4.354

6.  Synthesis of 2,3-allenylamides utilizing [1,2]-phospha-Brook rearrangement and their application to gold-catalyzed cycloisomerization providing 2-aminofuran derivatives.

Authors:  Azusa Kondoh; Sho Ishikawa; Takuma Aoki; Masahiro Terada
Journal:  Chem Commun (Camb)       Date:  2016-10-13       Impact factor: 6.222

7.  Cyanide ion promoted addition of acyl phosphonates to ethyl cyanoformate: synthesis of tertiary carbinols via tandem carbon-carbon bond formations.

Authors:  Ayhan S Demir; Barbaros Reis; Omer Reis; Serkan Eymür; Mehmet Göllü; Servet Tural; Gülüzar Saglam
Journal:  J Org Chem       Date:  2007-08-23       Impact factor: 4.354

8.  Cinchona alkaloid-based chiral catalysts act as highly efficient multifunctional organocatalysts for the asymmetric conjugate addition of malonates to nitroolefins.

Authors:  Veeramanoharan Ashokkumar; Ayyanar Siva
Journal:  Org Biomol Chem       Date:  2015-08-26       Impact factor: 3.876

9.  Catalytic intermolecular aldehyde-ketone coupling via acyl phosphonates.

Authors:  Ayhan S Demir; Lker Esiringü; Mehmet Göllü; Omer Reis
Journal:  J Org Chem       Date:  2009-03-06       Impact factor: 4.354

10.  Bifunctional iminophosphorane organocatalysts for enantioselective synthesis: application to the ketimine nitro-Mannich reaction.

Authors:  Marta G Núñez; Alistair J M Farley; Darren J Dixon
Journal:  J Am Chem Soc       Date:  2013-11-06       Impact factor: 15.419
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