Literature DB >> 31082224

Nickel-Catalyzed Asymmetric C-Alkylation of Nitroalkanes: Synthesis of Enantioenriched β-Nitroamides.

Vijayarajan Devannah1, Rajgopal Sharma1, Donald A Watson1.   

Abstract

A general catalytic method for asymmetric C-alkylation of nitroalkanes using nickel catalysis is described. This method enables the formation of highly enantioenriched β-nitroamides from readily available α-bromoamides using mild reaction conditions that are compatible with a wide range of functional groups. When combined with subsequent reactions, this method allows access to highly enantioenriched products with nitrogen-bearing fully substituted carbon centers.

Entities:  

Year:  2019        PMID： 31082224      PMCID： PMC6547819          DOI： 10.1021/jacs.9b04175

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  24 in total

1.  Chiral Brønsted base-promoted nitroalkane alkylation: enantioselective synthesis of sec-alkyl-3-substituted indoles.

Authors:  Mark C Dobish; Jeffrey N Johnston
Journal:  Org Lett       Date:  2010-11-19       Impact factor: 6.005

Review 2.  Nitro-Mannich reaction.

Authors:  Adam Noble; James C Anderson
Journal:  Chem Rev       Date:  2013-03-05       Impact factor: 60.622

3.  Ligand redox effects in the synthesis, electronic structure, and reactivity of an alkyl-alkyl cross-coupling catalyst.

Authors:  Gavin D Jones; Jason L Martin; Chris McFarland; Olivia R Allen; Ryan E Hall; Aireal D Haley; R Jacob Brandon; Tatyana Konovalova; Patrick J Desrochers; Peter Pulay; David A Vicic
Journal:  J Am Chem Soc       Date:  2006-10-11       Impact factor: 15.419

4.  Bifunctional primary amine-thioureas in asymmetric organocatalysis.

Authors:  Olga V Serdyuk; Christina M Heckel; Svetlana B Tsogoeva
Journal:  Org Biomol Chem       Date:  2013-11-07       Impact factor: 3.876

5.  Highly diastereo- and enantioselective formal conjugate addition of nitroalkanes to nitroalkenes by chiral ammonium bifluoride catalysis.

Authors:  Takashi Ooi; Saki Takada; Kanae Doda; Keiji Maruoka
Journal:  Angew Chem Int Ed Engl       Date:  2006-11-20       Impact factor: 15.336

6.  Ion-paired chiral ligands for asymmetric palladium catalysis.

Authors:  Kohsuke Ohmatsu; Mitsunori Ito; Tomoatsu Kunieda; Takashi Ooi
Journal:  Nat Chem       Date:  2012-04-01       Impact factor: 24.427

7.  Asymmetric Suzuki cross-couplings of activated secondary alkyl electrophiles: arylations of racemic alpha-chloroamides.

Authors:  Pamela M Lundin; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2010-08-18       Impact factor: 15.419

8.  Benzylation of nitroalkanes using copper-catalyzed thermal redox catalysis: toward the facile C-alkylation of nitroalkanes.

Authors:  Peter G Gildner; Amber A S Gietter; Di Cui; Donald A Watson
Journal:  J Am Chem Soc       Date:  2012-06-12       Impact factor: 15.419

9.  Enantioselective aldehyde alpha-nitroalkylation via oxidative organocatalysis.

Authors:  Jonathan E Wilson; Anthony D Casarez; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2009-08-19       Impact factor: 15.419

10.  Organocatalytic enantioselective synthesis of 2,3-allenoates by intermolecular addition of nitroalkanes to activated enynes.

Authors:  Hui Qian; Xiuzhao Yu; Junliang Zhang; Jianwei Sun
Journal:  J Am Chem Soc       Date:  2013-11-21       Impact factor: 15.419
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  2 in total

1.  DFT insight into asymmetric alkyl-alkyl bond formation via nickel-catalysed enantioconvergent reductive coupling of racemic electrophiles with olefins.

Authors:  Chao-Shen Zhang; Bei-Bei Zhang; Liang Zhong; Xiang-Yu Chen; Zhi-Xiang Wang
Journal:  Chem Sci       Date:  2022-02-25       Impact factor: 9.825

2.  Enantioselective Hydrocarbamoylation of Alkenes.

Authors:  Sheng Feng; Yuyang Dong; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2022-06-23       Impact factor: 16.823
  2 in total

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