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Literature DB >> 28825816

Radical Redox-Relay Catalysis: Formal [3+2] Cycloaddition of N-Acylaziridines and Alkenes.

Wei Hao¹, Xiangyu Wu¹, James Z Sun¹, Juno C Siu¹, Samantha N MacMillan¹, Song Lin¹.

Abstract

We report Ti-catalyzed radical formal [3+2] cycloadditions of N-acylaziridines and alkenes. This method provides an efficient approach to the synthesis of pyrrolidines, structural units prevalent in bioactive compounds and organocatalysts, from readily available starting materials. The overall redox-neutral reaction was achieved via a redox-relay mechanism, which harnesses radical intermediates for selective C-N bond cleavage and formation.

Entities: Chemical

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Year: 2017 PMID： 28825816 DOI： 10.1021/jacs.7b06723

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

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Cited

21 in total

1. Asymmetric Induction and Enantiodivergence in Catalytic Radical C-H Amination via Enantiodifferentiative H-Atom Abstraction and Stereoretentive Radical Substitution.

Authors: Kai Lang; Sebastian Torker; Lukasz Wojtas; X Peter Zhang
Journal: J Am Chem Soc Date: 2019-07-29 Impact factor: 15.419

2. Enantioselective Intermolecular Radical C-H Amination.

Authors: Li-Mei Jin; Pan Xu; Jingjing Xie; X Peter Zhang
Journal: J Am Chem Soc Date: 2020-11-25 Impact factor: 15.419

3. Rh(II)-Catalyzed Nitrene-Transfer [5 + 1] Cycloadditions of Aryl-Substituted Vinylcyclopropanes.

Authors: Logan A Combee; Shea L Johnson; Julie E Laudenschlager; Michael K Hilinski
Journal: Org Lett Date: 2019-03-25 Impact factor: 6.005

4. Is the Electrophilicity of the Metal Nitrene the Sole Predictor of Metal-Mediated Nitrene Transfer to Olefins? Secondary Contributing Factors as Revealed by a Library of High-Spin Co(II) Reagents.

Authors: Anshika Kalra; Vivek Bagchi; Patrina Paraskevopoulou; Purak Das; Lin Ai; Yiannis Sanakis; Grigorios Raptopoulos; Sudip Mohapatra; Amitava Choudhury; Zhicheng Sun; Thomas R Cundari; Pericles Stavropoulos
Journal: Organometallics Date: 2021-06-04 Impact factor: 3.876

Radical Redox-Relay Catalysis: Formal [3+2] Cycloaddition of N-Acylaziridines and Alkenes.

1. Asymmetric Induction and Enantiodivergence in Catalytic Radical C-H Amination via Enantiodifferentiative H-Atom Abstraction and Stereoretentive Radical Substitution.

2. Enantioselective Intermolecular Radical C-H Amination.

3. Rh(II)-Catalyzed Nitrene-Transfer [5 + 1] Cycloadditions of Aryl-Substituted Vinylcyclopropanes.

4. Is the Electrophilicity of the Metal Nitrene the Sole Predictor of Metal-Mediated Nitrene Transfer to Olefins? Secondary Contributing Factors as Revealed by a Library of High-Spin Co(II) Reagents.

5. Enantioselective Radical Cyclization for Construction of 5-Membered Ring Structures by Metalloradical C-H Alkylation.

6. Catalytic Radical Process for Enantioselective Amination of C(sp³ )-H Bonds.

7. Ti-Catalyzed Radical Alkylation of Secondary and Tertiary Alkyl Chlorides Using Michael Acceptors.

8. Enantioconvergent Amination of Racemic Tertiary C-H Bonds.

9. Enantioselective Radical Construction of 5-Membered Cyclic Sulfonamides by Metalloradical C-H Amination.

10. New Catalytic Radical Process Involving 1,4-Hydrogen Atom Abstraction: Asymmetric Construction of Cyclobutanones.