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Literature DB >> 25668687

Enantioselective conjugate additions of α-amino radicals via cooperative photoredox and Lewis acid catalysis.

Laura Ruiz Espelt¹, Iain S McPherson, Eric M Wiensch, Tehshik P Yoon.

Abstract

We report the highly enantioselective addition of photogenerated α-amino radicals to Michael acceptors. This method features a dual-catalyst protocol that combines transition metal photoredox catalysis with chiral Lewis acid catalysis. The combination of these two powerful modes of catalysis provides an effective, general strategy to generate and control the reactivity of photogenerated reactive intermediates.

Entities: Chemical Gene

Mesh：

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Year: 2015 PMID： 25668687 PMCID： PMC4547529 DOI： 10.1021/ja512746q

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

23 in total

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Journal: Nature Date: 2005-08-25 Impact factor: 49.962

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Journal: Chem Rev Date: 2008-02-27 Impact factor: 60.622

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Journal: Org Lett Date: 2012-01-19 Impact factor: 6.005

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Authors: Zhiwei Zuo; Derek T Ahneman; Lingling Chu; Jack A Terrett; Abigail G Doyle; David W C MacMillan
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Authors: Hui-Wen Shih; Mark N Vander Wal; Rebecca L Grange; David W C MacMillan
Journal: J Am Chem Soc Date: 2010-10-06 Impact factor: 15.419

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Authors: Daniel A DiRocco; Tomislav Rovis
Journal: J Am Chem Soc Date: 2012-05-02 Impact factor: 15.419

8. Enantioselective photoredox catalysis enabled by proton-coupled electron transfer: development of an asymmetric aza-pinacol cyclization.

Authors: Lydia J Rono; Hatice G Yayla; David Y Wang; Michael F Armstrong; Robert R Knowles
Journal: J Am Chem Soc Date: 2013-11-13 Impact factor: 15.419

9. Synthesis of nitrogen heterocycles via α-aminoalkyl radicals generated from α-silyl secondary amines under visible light irradiation.

Authors: Kazunari Nakajima; Mai Kitagawa; Yuya Ashida; Yoshihiro Miyake; Yoshiaki Nishibayashi
Journal: Chem Commun (Camb) Date: 2014-08-18 Impact factor: 6.222

10. Oxygen switch in visible-light photoredox catalysis: radical additions and cyclizations and unexpected C-C-bond cleavage reactions.

Authors: Shaoqun Zhu; Arindam Das; Lan Bui; Hanjun Zhou; Dennis P Curran; Magnus Rueping
Journal: J Am Chem Soc Date: 2013-01-18 Impact factor: 15.419

41 in total

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Journal: J Am Chem Soc Date: 2017-11-16 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. Photoredox-Catalyzed Site-Selective α-C(sp³ )-H Alkylation of Primary Amine Derivatives.

Authors: Melissa A Ashley; Chiaki Yamauchi; John C K Chu; Shinya Otsuka; Hideki Yorimitsu; Tomislav Rovis
Journal: Angew Chem Int Ed Engl Date: 2019-02-15 Impact factor: 15.336

4. Enantioselective Photocatalytic [3 + 2] Cycloadditions of Aryl Cyclopropyl Ketones.

Authors: Adrian G Amador; Evan M Sherbrook; Tehshik P Yoon
Journal: J Am Chem Soc Date: 2016-03-29 Impact factor: 15.419

5. Enantioselective photochemistry through Lewis acid-catalyzed triplet energy transfer.

Authors: Travis R Blum; Zachary D Miller; Desiree M Bates; Ilia A Guzei; Tehshik P Yoon
Journal: Science Date: 2016-12-16 Impact factor: 47.728

6. Iterative assembly line synthesis of polypropionates with full stereocontrol.

Authors: Teerawut Bootwicha; Julian M Feilner; Eddie L Myers; Varinder K Aggarwal
Journal: Nat Chem Date: 2017-04-10 Impact factor: 24.427

7. Cross-Electrophile Coupling of Unactivated Alkyl Chlorides.

Authors: Holt A Sakai; Wei Liu; Chi Chip Le; David W C MacMillan
Journal: J Am Chem Soc Date: 2020-06-26 Impact factor: 15.419

8. Highly Diastereoselective Functionalization of Piperidines by Photoredox-Catalyzed α-Amino C-H Arylation and Epimerization.

Authors: Morgan M Walker; Brian Koronkiewicz; Shuming Chen; K N Houk; James M Mayer; Jonathan A Ellman
Journal: J Am Chem Soc Date: 2020-04-24 Impact factor: 15.419

9. Radical Hydroarylation of Functionalized Olefins and Mechanistic Investigation of Photocatalytic Pyridyl Radical Reactions.

Authors: Ciaran P Seath; David B Vogt; Zihao Xu; Allyson J Boyington; Nathan T Jui
Journal: J Am Chem Soc Date: 2018-11-05 Impact factor: 15.419

10. α-Arylation/Heteroarylation of Chiral α-Aminomethyltrifluoroborates by Synergistic Iridium Photoredox/Nickel Cross-Coupling Catalysis.

Authors: Mirna El Khatib; Ricardo Augusto Massarico Serafim; Gary A Molander
Journal: Angew Chem Int Ed Engl Date: 2015-11-23 Impact factor: 15.336