Literature DB >> 29465998

Diastereo- and Enantioselective Formal [3 + 2] Cycloaddition of Cyclopropyl Ketones and Alkenes via Ti-Catalyzed Radical Redox Relay.

Wei Hao1, Johannes H Harenberg1,2, Xiangyu Wu1, Samantha N MacMillan1, Song Lin1,3.   

Abstract

We report a stereoselective formal [3 + 2] cycloaddition of cyclopropyl ketones and radical-acceptor alkenes to form polysubstituted cyclopentane derivatives. Catalyzed by a chiral Ti(salen) complex, the cycloaddition occurs via a radical redox-relay mechanism and constructs two C-C bonds and two contiguous stereogenic centers with generally excellent diastereo- and enantioselectivity.

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Year:  2018        PMID： 29465998     DOI： 10.1021/jacs.7b13710

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


  12 in total

1.  Mechanistic Studies Inform Design of Improved Ti(salen) Catalysts for Enantioselective [3 + 2] Cycloaddition.

Authors:  Sophia G Robinson; Xiangyu Wu; Binyang Jiang; Matthew S Sigman; Song Lin
Journal:  J Am Chem Soc       Date:  2020-10-16       Impact factor: 15.419

2.  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

3.  Synthetic Studies toward the Hamigerans with a 6-7-5 Tricyclic Core.

Authors:  Baiyang Jiang; Mingji Dai
Journal:  Org Lett       Date:  2020-05-13       Impact factor: 6.005

4.  CdS Quantum Dots as Potent Photoreductants for Organic Chemistry Enabled by Auger Processes.

Authors:  Jonas K Widness; Daniel G Enny; Kaelyn S McFarlane-Connelly; Mahilet T Miedenbauer; Todd D Krauss; Daniel J Weix
Journal:  J Am Chem Soc       Date:  2022-06-30       Impact factor: 16.383

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

Authors:  Xiangyu Wu; Yejin Chang; Song Lin
Journal:  Chem       Date:  2022-07-01       Impact factor: 25.832

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

Authors:  Chaoqun Li; Kai Lang; Hongjian Lu; Yang Hu; Xin Cui; Lukasz Wojtas; X Peter Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2018-11-16       Impact factor: 15.336

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

Authors:  Xiangyu Wu; Wei Hao; Ke-Yin Ye; Binyang Jiang; Gisselle Pombar; Zhidong Song; Song Lin
Journal:  J Am Chem Soc       Date:  2018-10-26       Impact factor: 15.419

Review 8.  Exploiting attractive non-covalent interactions for the enantioselective catalysis of reactions involving radical intermediates.

Authors:  Rupert S J Proctor; Avene C Colgan; Robert J Phipps
Journal:  Nat Chem       Date:  2020-10-22       Impact factor: 24.427

9.  SmI2-Catalyzed Intermolecular Coupling of Cyclopropyl Ketones and Alkynes: A Link between Ketone Conformation and Reactivity.

Authors:  Soumitra Agasti; Nicholas A Beattie; Joseph J W McDouall; David J Procter
Journal:  J Am Chem Soc       Date:  2021-02-25       Impact factor: 15.419

10.  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
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