Literature DB >> 22514037

Stereoselective hydrofluorination of ynamides: a straightforward synthesis of novel α-fluoroenamides.

Guillaume Compain1, Kevin Jouvin, Agnès Martin-Mingot, Gwilherm Evano, Jérome Marrot, Sébastien Thibaudeau.   

Abstract

α-Fluoroenamides, potent rigid fluorinated bioisosters of ureas, have been synthesized by a highly regio- and stereo-selective hydrofluorination of ynamides in anhydrous HF. This reaction provides the first general entry to α-fluoroenamides and can easily be applied to a wide range of substrates. This journal is © The Royal Society of Chemistry 2012

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Year:  2012        PMID： 22514037     DOI： 10.1039/c2cc31768k

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  10 in total

1.  (Radio)fluoroclick Reaction Enabled by a Hydrogen-Bonding Cluster.

Authors:  Xiaojun Zeng; Junling Li; Chin K Ng; Gerald B Hammond; Bo Xu
Journal:  Angew Chem Int Ed Engl       Date:  2018-02-13       Impact factor: 15.336

2.  Regio- and Stereoselective Synthesis of 1,2-Dihaloalkenes Using In-Situ-Generated ICl, IBr, BrCl, I2, and Br2.

Authors:  Xiaojun Zeng; Shiwen Liu; Yuhao Yang; Yi Yang; Gerald B Hammond; Bo Xu
Journal:  Chem       Date:  2020-04-09       Impact factor: 22.804

3.  Stereodivergent Alkyne Hydrofluorination Using Protic Tetrafluoroborates as Tunable Reagents.

Authors:  Rui Guo; Xiaotian Qi; Hengye Xiang; Paul Geaneotes; Ruihan Wang; Peng Liu; Yi-Ming Wang
Journal:  Angew Chem Int Ed Engl       Date:  2020-07-14       Impact factor: 15.336

4.  Metal-free, Regio-, and Stereo-Controlled Hydrochlorination and Hydrobromination of Ynones and Ynamides.

Authors:  Xiaojun Zeng; Zhichao Lu; Shiwen Liu; Gerald B Hammond; Bo Xu
Journal:  J Org Chem       Date:  2017-12-07       Impact factor: 4.354

5.  A HF Loaded Lewis-Acidic Aluminium Chlorofluoride for Hydrofluorination Reactions.

Authors:  Maëva-Charlotte Kervarec; Erhard Kemnitz; Gudrun Scholz; Svemir Rudić; Thomas Braun; Christian Jäger; Adam A L Michalchuk; Franziska Emmerling
Journal:  Chemistry       Date:  2020-05-26       Impact factor: 5.236

6.  Fluoroenesulphonamides: N-sulphonylurea isosteres showing nanomolar selective cancer-related transmembrane human carbonic anhydrase inhibition.

Authors:  Benoit Métayer; Andrea Angeli; Agnès Mingot; Kévin Jouvin; Gwilherm Evano; Claudiu T Supuran; Sébastien Thibaudeau
Journal:  J Enzyme Inhib Med Chem       Date:  2018-12       Impact factor: 5.051

7.  Chemo- and regio-divergent access to fluorinated 1-alkyl and 1-acyl triazenes from alkynyl triazenes.

Authors:  Jin-Fay Tan; Carl Thomas Bormann; Kay Severin; Nicolai Cramer
Journal:  Chem Sci       Date:  2022-02-09       Impact factor: 9.825

8.  Regio- and stereoselective carbometallation reactions of N-alkynylamides and sulfonamides.

Authors:  Yury Minko; Morgane Pasco; Helena Chechik; Ilan Marek
Journal:  Beilstein J Org Chem       Date:  2013-03-13       Impact factor: 2.883

9.  Harnessing the Electrophilicity of Keteniminium Ions: A Simple and Straightforward Entry to Tetrahydropyridines and Piperidines from Ynamides.

Authors:  Morgan Lecomte; Gwilherm Evano
Journal:  Angew Chem Int Ed Engl       Date:  2016-03-02       Impact factor: 15.336

Review 10.  Synthesis and Therapeutic Applications of Iminosugars in Cystic Fibrosis.

Authors:  Anna Esposito; Daniele D'Alonzo; Maria De Fenza; Eliana De Gregorio; Anna Tamanini; Giuseppe Lippi; Maria Cristina Dechecchi; Annalisa Guaragna
Journal:  Int J Mol Sci       Date:  2020-05-09       Impact factor: 5.923
  10 in total

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