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Literature DB >> 21848264

Enantioselective α-arylation of N-acyloxazolidinones with copper(II)-bisoxazoline catalysts and diaryliodonium salts.

Aurélien Bigot¹, Alice E Williamson, Matthew J Gaunt.

Abstract

A new strategy for the catalytic enantioselective α-arylation of N-acyloxazolidinones with chiral copper(II)-bisoxazoline complexes and diaryliodonium salts is described. The mild catalytic conditions are operationally simple, produce valuable synthetic building blocks in excellent yields and enantioselectivities, and can be applied to the synthesis of important nonsteroidal anti-inflammatory agents and their analogues.

Entities: Chemical

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Year: 2011 PMID： 21848264 DOI： 10.1021/ja206047h

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

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Cited

24 in total

1. Concise Total Synthesis of (+)-Asperazine, (+)-Pestalazine A, and (+)-iso-Pestalazine A. Structure Revision of (+)-Pestalazine A.

Authors: Richard P Loach; Owen S Fenton; Mohammad Movassaghi
Journal: J Am Chem Soc Date: 2016-01-19 Impact factor: 15.419

2. 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

3. Direct C-H α-Arylation of Enones with ArI(O₂CR)₂ Reagents.

Authors: Felipe Cesar Sousa E Silva; Nguyen T Van; Sarah E Wengryniuk
Journal: J Am Chem Soc Date: 2019-12-27 Impact factor: 15.419

4. Enantioselective α-alkenylation of aldehydes with boronic acids via the synergistic combination of copper(II) and amine catalysis.

Authors: Jason M Stevens; David W C MacMillan
Journal: J Am Chem Soc Date: 2013-08-05 Impact factor: 15.419

9. Enantioselective and Regiodivergent Copper-Catalyzed Electrophilic Arylation of Allylic Amides with Diaryliodonium Salts.

Authors: Elise Cahard; Henry P J Male; Matthieu Tissot; Matthew J Gaunt
Journal: J Am Chem Soc Date: 2015-06-19 Impact factor: 15.419

10. Efficient synthesis of 3H-indoles enabled by the lead-mediated α-arylation of β-ketoesters or γ-lactams using aryl azides.

Authors: Fei Zhou; Tom G Driver
Journal: Org Lett Date: 2014-05-27 Impact factor: 6.005

Enantioselective α-arylation of N-acyloxazolidinones with copper(II)-bisoxazoline catalysts and diaryliodonium salts.

1. Concise Total Synthesis of (+)-Asperazine, (+)-Pestalazine A, and (+)-iso-Pestalazine A. Structure Revision of (+)-Pestalazine A.

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

3. Direct C-H α-Arylation of Enones with ArI(O₂CR)₂ Reagents.

4. Enantioselective α-alkenylation of aldehydes with boronic acids via the synergistic combination of copper(II) and amine catalysis.

5. Design, Synthesis, and Optimization of Balanced Dual NK1/NK3 Receptor Antagonists.

6. Enantioselective copper-catalyzed construction of aryl pyrroloindolines via an arylation-cyclization cascade.

7. Silyl ketene imines: highly versatile nucleophiles for catalytic, asymmetric synthesis.

8. The ketene-surrogate coupling: catalytic conversion of aryl iodides into aryl ketenes through ynol ethers.

9. Enantioselective and Regiodivergent Copper-Catalyzed Electrophilic Arylation of Allylic Amides with Diaryliodonium Salts.

10. Efficient synthesis of 3H-indoles enabled by the lead-mediated α-arylation of β-ketoesters or γ-lactams using aryl azides.