Literature DB >> 26066512

A Nucleophilic Strategy for Enantioselective Intermolecular α-Amination: Access to Enantioenriched α-Arylamino Ketones.

Dillon H Miles1,2, Joan Guasch1,2, F Dean Toste1,2.   

Abstract

The enantioselective addition of anilines to azoalkenes was accomplished through the use of a chiral phosphoric acid catalyst. The resulting α-arylamino hydrazones were obtained in good yields and excellent enantioselectivities and provide access to enantioenriched α-arylamino ketones. A serendipitous kinetic resolution of racemic α-arylamino hydrazones is also described.

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Year:  2015        PMID: 26066512      PMCID: PMC5152760          DOI: 10.1021/jacs.5b04518

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


  47 in total

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Journal:  J Org Chem       Date:  2014-08-29       Impact factor: 4.354

2.  Asymmetric cross-dehydrogenative coupling enabled by the design and application of chiral triazole-containing phosphoric acids.

Authors:  Andrew J Neel; Jörg P Hehn; Pascal F Tripet; F Dean Toste
Journal:  J Am Chem Soc       Date:  2013-09-11       Impact factor: 15.419

Review 3.  Recent advances in catalytic, enantioselective alpha aminations and alpha oxygenations of carbonyl compounds.

Authors:  Jacob M Janey
Journal:  Angew Chem Int Ed Engl       Date:  2005-07-11       Impact factor: 15.336

4.  Metallic organophosphates as catalysts in asymmetric synthesis: a return journey.

Authors:  Alejandro Parra; Silvia Reboredo; Ana M Martín Castro; José Alemán
Journal:  Org Biomol Chem       Date:  2012-05-09       Impact factor: 3.876

5.  Enantioselective alpha-amination of 1,3-dicarbonyl compounds using squaramide derivatives as hydrogen bonding catalysts.

Authors:  Hideyuki Konishi; Tin Yiu Lam; Jeremiah P Malerich; Viresh H Rawal
Journal:  Org Lett       Date:  2010-05-07       Impact factor: 6.005

6.  Asymmetric counteranion-directed catalysis: concept, definition, and applications.

Authors:  Manuel Mahlau; Benjamin List
Journal:  Angew Chem Int Ed Engl       Date:  2012-11-28       Impact factor: 15.336

7.  Chiral calcium-BINOL phosphate catalyzed diastereo- and enantioselective synthesis of syn-1,2-disubstituted 1,2-diamines: scope and mechanistic studies.

Authors:  Claudia Lalli; Audrey Dumoulin; Clément Lebée; Fleur Drouet; Vincent Guérineau; David Touboul; Vincent Gandon; Jieping Zhu; Géraldine Masson
Journal:  Chemistry       Date:  2014-11-21       Impact factor: 5.236

8.  Practical approach for asymmetric hydroxyamination of aldehydes with in situ generated nitrosocarbonyl compounds: application to one-pot synthesis of chiral allylamines.

Authors:  Taichi Kano; Fumitaka Shirozu; Keiji Maruoka
Journal:  Org Lett       Date:  2014-02-19       Impact factor: 6.005

9.  Proline-tetrazole-catalyzed enantioselective N-nitroso aldol reaction of aldehydes with in situ generated nitrosocarbonyl compounds.

Authors:  Biplab Maji; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2014-02-19       Impact factor: 15.336

10.  Enantioselective synthesis of piperidines through the formation of chiral mixed phosphoric acid acetals: experimental and theoretical studies.

Authors:  Zhankui Sun; Grace A Winschel; Paul M Zimmerman; Pavel Nagorny
Journal:  Angew Chem Int Ed Engl       Date:  2014-09-04       Impact factor: 15.336

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  5 in total

1.  Chemo- and Stereoselective Transition-Metal-Free Amination of Amides with Azides.

Authors:  Veronica Tona; Aurélien de la Torre; Mohan Padmanaban; Stefan Ruider; Leticia González; Nuno Maulide
Journal:  J Am Chem Soc       Date:  2016-06-28       Impact factor: 15.419

2.  Synthesis of γ-substituted carbonyl compounds from DMSO-mediated oxidation of enynamides: mechanistic insights and carbon- and hetero-functionalizations.

Authors:  Quynh H Nguyen; Nguyen H Nguyen; Hanbyul Kim; Seunghoon Shin
Journal:  Chem Sci       Date:  2019-08-12       Impact factor: 9.825

3.  Light-Driven Carbene Catalysis for the Synthesis of Aliphatic and α-Amino Ketones.

Authors:  Anna V Bay; Keegan P Fitzpatrick; Gisela A González-Montiel; Abdikani Omar Farah; Paul Ha-Yeon Cheong; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2021-07-14       Impact factor: 16.823

4.  Direct catalytic enantioselective amination of ketones for the formation of tri- and tetrasubstituted stereocenters.

Authors:  B M Trost; J S Tracy; T Saget
Journal:  Chem Sci       Date:  2018-02-14       Impact factor: 9.825

5.  Catalytic Asymmetric Formal [3+2] Cycloaddition of Azoalkenes with 3-Vinylindoles: Synthesis of 2,3-Dihydropyrroles.

Authors:  Guang-Jian Mei; Wenrui Zheng; Théo P Gonçalves; Xiwen Tang; Kuo-Wei Huang; Yixin Lu
Journal:  iScience       Date:  2020-01-31
  5 in total

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