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Literature DB >> 22486383

A simple method for asymmetric trifluoromethylation of N-acyl oxazolidinones via Ru-catalyzed radical addition to zirconium enolates.

Aaron T Herrmann¹, Lindsay L Smith, Armen Zakarian.

Abstract

A Ru-catalyzed direct thermal trifluoromethylation and perfluoroalkylation of N-acyloxazolidinones has been developed. The reaction is experimentally simple and requires inexpensive reagents while providing good yields of products with good levels of stereocontrol. Preliminary studies have shown notable compatibility with functional groups, aromatics, and certain heteroaromatic substituents. The described method provides a useful alternative for the synthesis of fluorinated materials in an experimentally convenient manner.

Entities: Chemical Disease Gene

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Year: 2012 PMID： 22486383 PMCID： PMC3375393 DOI： 10.1021/ja302552e

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

21 in total

1. Activation of C-F bonds in preference to C-I bonds: difluoromethylation of lithium enolates with trifluoromethyl iodide.

Authors: Koichi Mikami; Yuichi Tomita; Yoshimitsu Itoh
Journal: Angew Chem Int Ed Engl Date: 2010-05-17 Impact factor: 15.336

Review 2. Asymmetric fluorination, trifluoromethylation, and perfluoroalkylation reactions.

Authors: Jun-An Ma; Dominique Cahard
Journal: Chem Rev Date: 2004-12 Impact factor: 60.622

3. Facile radical trifluoromethylation of lithium enolates.

Authors: Yoshimitsu Itoh; Koichi Mikami
Journal: Org Lett Date: 2005-10-27 Impact factor: 6.005

4. Unconventional biradical character of titanium enolates.

Authors: I de P R Moreira; J M Bofill; J M Anglada; J G Solsona; J Nebot; P Romea; F Urpí
Journal: J Am Chem Soc Date: 2008-02-21 Impact factor: 15.419

5. Update 1 of: Asymmetric fluorination, trifluoromethylation, and perfluoroalkylation reactions.

Authors: Jun-An Ma; Dominique Cahard
Journal: Chem Rev Date: 2008-09 Impact factor: 60.622

6. The productive merger of iodonium salts and organocatalysis: a non-photolytic approach to the enantioselective alpha-trifluoromethylation of aldehydes.

Authors: Anna E Allen; David W C Macmillan
Journal: J Am Chem Soc Date: 2010-04-14 Impact factor: 15.419

7. Efficient total synthesis of dysidenin, dysidin, and barbamide.

Authors: Elizabeth A Ilardi; Armen Zakarian
Journal: Chem Asian J Date: 2011-06-22

8. Dual Ti-Ru catalysis in the direct radical haloalkylation of N-acyl oxazolidinones.

Authors: Zhenhua Gu; Aaron T Herrmann; Armen Zakarian
Journal: Angew Chem Int Ed Engl Date: 2011-06-17 Impact factor: 15.336

9. Direct carbon-carbon bond formation via chemoselective soft enolization of thioesters: a remarkably simple and versatile crossed-Claisen reaction applied to the synthesis of LY294002.

Authors: Guoqiang Zhou; Daniel Lim; Don M Coltart
Journal: Org Lett Date: 2008-08-06 Impact factor: 6.005

8. Regio- and Stereoselective Radical Perfluoroalkyltriflation of Alkynes Using Phenyl(perfluoroalkyl)iodonium Triflates.

Authors: Xi Wang; Armido Studer
Journal: Org Lett Date: 2017-05-18 Impact factor: 6.005

8 in total

A simple method for asymmetric trifluoromethylation of N-acyl oxazolidinones via Ru-catalyzed radical addition to zirconium enolates.

1. Activation of C-F bonds in preference to C-I bonds: difluoromethylation of lithium enolates with trifluoromethyl iodide.

Review 2. Asymmetric fluorination, trifluoromethylation, and perfluoroalkylation reactions.

3. Facile radical trifluoromethylation of lithium enolates.

4. Unconventional biradical character of titanium enolates.

5. Update 1 of: Asymmetric fluorination, trifluoromethylation, and perfluoroalkylation reactions.

6. The productive merger of iodonium salts and organocatalysis: a non-photolytic approach to the enantioselective alpha-trifluoromethylation of aldehydes.

7. Efficient total synthesis of dysidenin, dysidin, and barbamide.

8. Dual Ti-Ru catalysis in the direct radical haloalkylation of N-acyl oxazolidinones.

9. Direct carbon-carbon bond formation via chemoselective soft enolization of thioesters: a remarkably simple and versatile crossed-Claisen reaction applied to the synthesis of LY294002.

10. Synthesis, characterization and biological evaluation of 7 alpha-perfluoroalkylestradiol derivatives.

1. Synthesis and applications of α-trifluoromethylated alkylboron compounds.

2. Asymmetric photoredox transition-metal catalysis activated by visible light.

3. Rhodium-Catalyzed Enantioselective Radical Addition of CX₄ Reagents to Olefins.

4. Stereoselective α-Tertiary Alkylation of N-(Arylacetyl)oxazolidinones.

5. Trifluoromethylation of Heterocycles in Water at Room Temperature.

Review 6. Radicals: Reactive Intermediates with Translational Potential.

7. Copper-catalyzed trifluoromethylation of alkenes with an electrophilic trifluoromethylating reagent.

8. Regio- and Stereoselective Radical Perfluoroalkyltriflation of Alkynes Using Phenyl(perfluoroalkyl)iodonium Triflates.