Literature DB >> 23537339

Enantioselective iron-catalyzed azidation of β-keto esters and oxindoles.

Qing-Hai Deng1, Tim Bleith, Hubert Wadepohl, Lutz H Gade.   

Abstract

The first example of Fe-catalyzed enantioselective azidations of β-keto esters and oxindoles using a readily available N3-transfer reagent is reported. A number of α-azido-β-keto esters were obtained with up to 93% ee, and this methodology also generates 3-substitued 3-azidooxindoles with high enantioselectivities (up to 94%).

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Year:  2013        PMID: 23537339     DOI: 10.1021/ja402082p

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


  14 in total

1.  Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis.

Authors:  Robert Connon; Brendan Roche; Balaji V Rokade; Patrick J Guiry
Journal:  Chem Rev       Date:  2021-05-21       Impact factor: 60.622

2.  Enantioselective, Stereodivergent Hydroazidation and Hydroamination of Allenes Catalyzed by Acyclic Diaminocarbene (ADC) Gold(I) Complexes.

Authors:  Dimitri A Khrakovsky; Chuanzhou Tao; Miles W Johnson; Richard T Thornbury; Sophia L Shevick; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2016-04-20       Impact factor: 15.336

3.  Versatile Enantioselective Synthesis of Functionalized Lactones via Copper-Catalyzed Radical Oxyfunctionalization of Alkenes.

Authors:  Rong Zhu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2015-06-23       Impact factor: 15.419

4.  Three-Component Azidation of Styrene-Type Double Bonds: Light-Switchable Behavior of a Copper Photoredox Catalyst.

Authors:  Gabriele Fumagalli; Pauline T G Rabet; Scott Boyd; Michael F Greaney
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-26       Impact factor: 15.336

Review 5.  Metal-Catalysed Azidation of Organic Molecules.

Authors:  Monalisa Goswami; Bas de Bruin
Journal:  European J Org Chem       Date:  2016-12-22

Review 6.  Asymmetric Preparation of α-Quaternary Fluorinated β-keto Esters. Review.

Authors:  Albert Granados; Adelina Vallribera
Journal:  Molecules       Date:  2020-07-17       Impact factor: 4.411

7.  Divergent synthesis of chiral cyclic azides via asymmetric cycloaddition reactions of vinyl azides.

Authors:  Nuligonda Thirupathi; Fang Wei; Chen-Ho Tung; Zhenghu Xu
Journal:  Nat Commun       Date:  2019-07-18       Impact factor: 14.919

8.  Chiral cis-iron(ii) complexes with metal- and ligand-centered chirality for highly regio- and enantioselective alkylation of N-heteroaromatics.

Authors:  Jinhu Wei; Bei Cao; Chun-Wai Tse; Xiao-Yong Chang; Cong-Ying Zhou; Chi-Ming Che
Journal:  Chem Sci       Date:  2019-11-25       Impact factor: 9.825

9.  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

10.  Towards an Asymmetric Organocatalytic α-Azidation of β-Ketoesters.

Authors:  Maximilian Tiffner; Lotte Stockhammer; Johannes Schörgenhumer; Katharina Röser; Mario Waser
Journal:  Molecules       Date:  2018-05-11       Impact factor: 4.411

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