Literature DB >> 30287974

Enantioselective counter-anions in photoredox catalysis: the asymmetric cation radical Diels-Alder reaction.

Peter D Morse1, Tien M Nguyen1, Cole L Cruz1, David A Nicewicz1.   

Abstract

Control of absolute stereochemistry in radical and ion radical transformations is a major challenge in synthetic chemistry. Herein, we report the design of a photoredox catalyst system comprised of an oxidizing pyrilium salt bearing a chiral N-triflyl phosphoramide anion. This class of chiral organic photoredox catalysts is able to catalyze the formation of cation radical-mediated Diels-Alder transformations in up to 75:25 e.r. in both intramolecular and intermolecular examples.

Entities:  

Keywords:  catalysis; chiral anion; cycloaddition; enantioselective; photoredox

Year:  2018        PMID： 30287974      PMCID： PMC6166882          DOI： 10.1016/j.tet.2018.03.052

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  19 in total

1.  An aromatic ion platform for enantioselective Brønsted acid catalysis.

Authors:  Chirag D Gheewala; Bridget E Collins; Tristan H Lambert
Journal:  Science       Date:  2016-02-26       Impact factor: 47.728

2.  Asymmetric counteranion-directed catalysis: concept, definition, and applications.

Authors:  Manuel Mahlau; Benjamin List
Journal:  Angew Chem Int Ed Engl       Date:  2012-11-28       Impact factor: 15.336

Review 3.  Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

Authors:  Christopher K Prier; Danica A Rankic; David W C MacMillan
Journal:  Chem Rev       Date:  2013-03-19       Impact factor: 60.622

4.  A dual-catalysis approach to enantioselective [2 + 2] photocycloadditions using visible light.

Authors:  Juana Du; Kazimer L Skubi; Danielle M Schultz; Tehshik P Yoon
Journal:  Science       Date:  2014-04-25       Impact factor: 47.728

5.  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

6.  Organic Photoredox Catalysis.

Authors:  Nathan A Romero; David A Nicewicz
Journal:  Chem Rev       Date:  2016-06-10       Impact factor: 60.622

7.  Enantioselective α-Alkylation of Aldehydes by Photoredox Organocatalysis: Rapid Access to Pharmacophore Fragments from β-Cyanoaldehydes.

Authors:  Eric R Welin; Alexander A Warkentin; Jay C Conrad; David W C MacMillan
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-30       Impact factor: 15.336

8.  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

9.  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

10.  Chromium photocatalysis: accessing structural complements to Diels-Alder adducts with electron-deficient dienophiles.

Authors:  Susan M Stevenson; Robert F Higgins; Matthew P Shores; Eric M Ferreira
Journal:  Chem Sci       Date:  2016-09-12       Impact factor: 9.825
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  13 in total

1.  Discovery and Elucidation of Counteranion Dependence in Photoredox Catalysis.

Authors:  Elliot P Farney; Steven J Chapman; Wesley B Swords; Marco D Torelli; Robert J Hamers; Tehshik P Yoon
Journal:  J Am Chem Soc       Date:  2019-04-02       Impact factor: 15.419

Review 2.  Recent Trends in Photocatalytic Enantioselective Reactions.

Authors:  Renu Verma; Palvi Jindal; Jagdish Prasad; S L Kothari; Narendra Pal Lamba; Anshu Dandia; Rama Kanwar Khangarot; Manmohan Singh Chauhan
Journal:  Top Curr Chem (Cham)       Date:  2022-09-16

3.  Enantioselective Hydroamination of Alkenes with Sulfonamides Enabled by Proton-Coupled Electron Transfer.

Authors:  Casey B Roos; Joachim Demaerel; David E Graff; Robert R Knowles
Journal:  J Am Chem Soc       Date:  2020-03-20       Impact factor: 15.419

Review 4.  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

Review 5.  Chiral Photocatalyst Structures in Asymmetric Photochemical Synthesis.

Authors:  Matthew J Genzink; Jesse B Kidd; Wesley B Swords; Tehshik P Yoon
Journal:  Chem Rev       Date:  2021-10-04       Impact factor: 60.622

6.  Photo-Organocatalytic Enantioselective Radical Cascade Reactions of Unactivated Olefins.

Authors:  Pablo Bonilla; Yannick P Rey; Catherine M Holden; Paolo Melchiorre
Journal:  Angew Chem Int Ed Engl       Date:  2018-08-31       Impact factor: 15.336

7.  Flavylium Salts: A Blooming Core for Bioinspired Ionic Liquid Crystals.

Authors:  Robert Forschner; Jakob Knelles; Korinna Bader; Carsten Müller; Wolfgang Frey; Andreas Köhn; Yann Molard; Frank Giesselmann; Sabine Laschat
Journal:  Chemistry       Date:  2019-09-18       Impact factor: 5.236

8.  A Computational and Experimental Investigation of the Origin of Selectivity in the Chiral Phosphoric Acid Catalyzed Enantioselective Minisci Reaction.

Authors:  Kristaps Ermanis; Avene C Colgan; Rupert S J Proctor; Barbara W Hadrys; Robert J Phipps; Jonathan M Goodman
Journal:  J Am Chem Soc       Date:  2020-11-30       Impact factor: 15.419

9.  Continuous-Flow Synthesis of Pyrylium Tetrafluoroborates: Application to Synthesis of Katritzky Salts and Photoinduced Cationic RAFT Polymerization.

Authors:  Carlo Sambiagio; Matteo Ferrari; Koen van Beurden; Nicola Della Ca'; Jack van Schijndel; Timothy Noël
Journal:  Org Lett       Date:  2021-03-02       Impact factor: 6.005

Review 10.  Construction of Chiral Cyclic Compounds Enabled by Enantioselective Photocatalysis.

Authors:  Bo Xu; Xiaotian Shi; Xiang Liu; Hua Cao
Journal:  Molecules       Date:  2022-01-07       Impact factor: 4.411
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