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Literature DB >> 28833905

Titanocene-Catalyzed Radical Opening of N-Acylated Aziridines.

Yong-Qiang Zhang¹, Elisabeth Vogelsang¹, Zheng-Wang Qu², Stefan Grimme², Andreas Gansäuer¹.

Abstract

Aziridines activated by N-acylation are opened to the higher substituted radical through electron transfer from titanocene(III) complexes in a novel catalytic reaction. This reaction is applicable in conjugate additions, reductions, and cyclizations and suited for the construction of quaternary carbon centers. The concerted mechanism of the ring opening is indicated by DFT calculations.

Entities: Chemical Disease

Keywords: aziridines; conjugate addition; radical ring opening; reduction; titanocenes

Year: 2017 PMID： 28833905 DOI： 10.1002/anie.201707673

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

9 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

8. Enantioselective radical process for synthesis of chiral indolines by metalloradical alkylation of diverse C(sp³)-H bonds.

Authors: Xin Wen; Yong Wang; X Peter Zhang
Journal: Chem Sci Date: 2018-05-14 Impact factor: 9.825

9. Design Platform for Sustainable Catalysis with Radicals: Electrochemical Activation of Cp₂ TiCl₂ for Catalysis Unveiled.

Authors: Tobias Hilche; Philip H Reinsberg; Sven Klare; Theresa Liedtke; Luise Schäfer; Andreas Gansäuer
Journal: Chemistry Date: 2021-01-12 Impact factor: 5.236

9 in total

Titanocene-Catalyzed Radical Opening of N-Acylated Aziridines.

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

2. Titanium Radical Redox Catalysis: Recent Innovations in Catalysts, Reactions, and Modes of Activation.

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

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

5. Theoretical investigation of the regioselective ring opening of 2-methylaziridine. Lewis acid effect.

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

7. Titanocene(III)-Catalyzed Precision Deuteration of Epoxides.

8. Enantioselective radical process for synthesis of chiral indolines by metalloradical alkylation of diverse C(sp³)-H bonds.

9. Design Platform for Sustainable Catalysis with Radicals: Electrochemical Activation of Cp₂ TiCl₂ for Catalysis Unveiled.