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 αn class="Chemical">-amino radicals to Michael acceptors. This method features a dual-catalyst protocol that combines tranpan>sition pan> class="Chemical">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.

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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

1.  Catalytic enantioselective reactions driven by photoinduced electron transfer.

Authors:  Andreas Bauer; Felix Westkämper; Stefan Grimme; Thorsten Bach
Journal:  Nature       Date:  2005-08-25       Impact factor: 49.962

2.  Photochemical reactions as key steps in organic synthesis.

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

3.  Visible light photoredox catalysis: generation and addition of N-aryltetrahydroisoquinoline-derived α-amino radicals to Michael acceptors.

Authors:  Paul Kohls; Deepak Jadhav; Ganesh Pandey; Oliver Reiser
Journal:  Org Lett       Date:  2012-01-19       Impact factor: 6.005

4.  Dual catalysis. Merging photoredox with nickel catalysis: coupling of α-carboxyl sp³-carbons with aryl halides.

Authors:  Zhiwei Zuo; Derek T Ahneman; Lingling Chu; Jack A Terrett; Abigail G Doyle; David W C MacMillan
Journal:  Science       Date:  2014-06-05       Impact factor: 47.728

5.  Enantioselective conjugate addition of hydroxylamines to pyrazolidinone acrylamides.

Authors:  M P Sibi; M Liu
Journal:  Org Lett       Date:  2001-12-27       Impact factor: 6.005

6.  Enantioselective α-benzylation of aldehydes via photoredox organocatalysis.

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

7.  Catalytic asymmetric α-acylation of tertiary amines mediated by a dual catalysis mode: N-heterocyclic carbene and photoredox catalysis.

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

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  41 in total

1.  Enantioselective Excited-State Photoreactions Controlled by a Chiral Hydrogen-Bonding Iridium Sensitizer.

Authors:  Kazimer L Skubi; Jesse B Kidd; Hoimin Jung; Ilia A Guzei; Mu-Hyun Baik; Tehshik P Yoon
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

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