Literature DB >> 31915785

Enantioselective catalytic synthesis of α-aryl-α-SCF3-β2,2-amino acids.

Andreas Eitzinger1, Jean-François Brière, Dominique Cahard, Mario Waser.   

Abstract

We herein report a novel entry towards chiral α-SCF3-β2,2-amino acids by carrying out the ammonium salt-catalyzed α-trifluoromethylthiolation of isoxazolidin-5-ones. This approach allowed for high enantioselectivities and high yields and the obtained heterocycles proved to be versatile platforms to access other targets of potential interest.

Entities:  

Year:  2020        PMID： 31915785      PMCID： PMC6989214          DOI： 10.1039/c9ob02666e

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  38 in total

1.  Design of N-spiro C2-symmetric chiral quaternary ammonium bromides as novel chiral phase-transfer catalysts: synthesis and application to practical asymmetric synthesis of alpha-amino acids.

Authors:  Takashi Ooi; Minoru Kameda; Keiji Maruoka
Journal:  J Am Chem Soc       Date:  2003-04-30       Impact factor: 15.419

Review 2.  Recent advances in cooperative ion pairing in asymmetric organocatalysis.

Authors:  Jean-François Brière; Sylvain Oudeyer; Vincent Dalla; Vincent Levacher
Journal:  Chem Soc Rev       Date:  2011-11-01       Impact factor: 54.564

3.  Visible-Light-Promoted Activation of Unactivated C(sp3)-H Bonds and Their Selective Trifluoromethylthiolation.

Authors:  Satobhisha Mukherjee; Biplab Maji; Adrian Tlahuext-Aca; Frank Glorius
Journal:  J Am Chem Soc       Date:  2016-12-09       Impact factor: 15.419

4.  Deciphering the Fluorine Code-The Many Hats Fluorine Wears in a Protein Environment.

Authors:  Allison Ann Berger; Jan-Stefan Völler; Nediljko Budisa; Beate Koksch
Journal:  Acc Chem Res       Date:  2017-08-12       Impact factor: 22.384

5.  Palladium-Catalyzed Asymmetric Allylic Alkylation of 4-Substituted Isoxazolidin-5-ones: Straightforward Access to β2,2 -Amino Acids.

Authors:  Marllon Nascimento de Oliveira; Stellios Arseniyadis; Janine Cossy
Journal:  Chemistry       Date:  2018-03-13       Impact factor: 5.236

6.  Exploiting β-Amino Acid Enolates in Direct Catalytic Diastereo- and Enantioselective C-C Bond-Forming Reactions.

Authors:  Jin-Sheng Yu; Hidetoshi Noda; Masakatsu Shibasaki
Journal:  Chemistry       Date:  2018-10-08       Impact factor: 5.236

7.  Approaches to Obtaining Fluorinated α-Amino Acids.

Authors:  Johann Moschner; Valentina Stulberg; Rita Fernandes; Susanne Huhmann; Jakob Leppkes; Beate Koksch
Journal:  Chem Rev       Date:  2019-08-22       Impact factor: 60.622

8.  1,4-Diazabicyclo[2.2.2]octane-Promoted Aminotrifluoromethylthiolation of α,β-Unsaturated Carbonyl Compounds: N-Trifluoromethylthio-4-nitrophthalimide Acts as Both the Nitrogen and SCF3 Sources.

Authors:  Qing Xiao; Qijie He; Juncheng Li; Jun Wang
Journal:  Org Lett       Date:  2015-12-10       Impact factor: 6.005

9.  Beta-amino acid-containing hybrid peptides--new opportunities in peptidomimetics.

Authors:  Marie-Isabel Aguilar; Anthony W Purcell; Romila Devi; Rebecca Lew; Jamie Rossjohn; A Ian Smith; Patrick Perlmutter
Journal:  Org Biomol Chem       Date:  2007-08-03       Impact factor: 3.876

10.  Electrophilic trifluoromethylthiolation of carbonyl compounds.

Authors:  Sébastien Alazet; Luc Zimmer; Thierry Billard
Journal:  Chemistry       Date:  2014-05-30       Impact factor: 5.236
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  5 in total

1.  Enantioselective Bifunctional Ammonium Salt-Catalyzed Syntheses of 3-CF3S-, 3-RS-, and 3-F-Substituted Isoindolinones.

Authors:  Andreas Eitzinger; Jan Otevrel; Victoria Haider; Antonio Macchia; Antonio Massa; Kirill Faust; Bernhard Spingler; Albrecht Berkessel; Mario Waser
Journal:  Adv Synth Catal       Date:  2021-02-17       Impact factor: 5.837

2.  Enantioselective organocatalytic syntheses of α-selenated α- and β-amino acid derivatives.

Authors:  Victoria Haider; Paul Zebrowski; Jessica Michalke; Uwe Monkowius; Mario Waser
Journal:  Org Biomol Chem       Date:  2022-01-26       Impact factor: 3.890

3.  Enantioselective Catalytic Synthesis of α-Halogenated α-Aryl-β2,2-amino Acid Derivatives.

Authors:  Paul Zebrowski; Isabella Eder; Andreas Eitzinger; Sharath Chandra Mallojjala; Mario Waser
Journal:  ACS Org Inorg Au       Date:  2021-09-24

4.  Ammonium Salt-Catalyzed Ring-Opening of Aryl-Aziridines with β-Keto Esters.

Authors:  Victoria Haider; Viktoria Kreuzer; Maximilian Tiffner; Bernhard Spingler; Mario Waser
Journal:  European J Org Chem       Date:  2020-07-15

Review 5.  Synthesis of complex unnatural fluorine-containing amino acids.

Authors:  William D G Brittain; Carissa M Lloyd; Steven L Cobb
Journal:  J Fluor Chem       Date:  2020-11       Impact factor: 2.050
  5 in total

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