Literature DB >> 36204304

Asymmetric Photocatalysis Enabled by Chiral Organocatalysts.

Wang Yao1, Emmanuel A Bazan Bergamino1, Ming-Yu Ngai1,2.   

Abstract

Visible-light photocatalysis has advanced as a versatile tool in organic synthesis. However, attaining precise stereocontrol in photocatalytic reactions has been a longstanding challenge due to undesired photochemical background reactions and the involvement of highly reactive radicals or radical ion intermediates generated under photocatalytic conditions. To address this problem and expand the synthetic utility of photocatalytic reactions, a number of innovative strategies, including mono- and dual-catalytic approaches, have recently emerged. Of these, exploiting chiral organocatalysis, such as enamine catalysis, iminium-ion catalysis, Brønsted acid/base catalysis, and N-heterocyclic carbene catalysis, to induce chirality transfer of photocatalytic reactions has been widely explored. This Review aims to provide a current, comprehensive overview of asymmetric photocatalytic reactions enabled by chiral organocatalysts published through June 2021. The substrate scope, advantages, limitations, and proposed reaction mechanisms of each reaction are discussed. This review should serve as a reference for the development of visible-light-induced asymmetric photocatalysis and promote the improvement of the chemical reactivity and stereoselectivity of these reactions.

Entities:  

Keywords:  Asymmetric catalysis; EDA complex; electron/energy transfer; organocatalysis; photoredox catalysis

Year:  2021        PMID: 36204304      PMCID: PMC9531867          DOI: 10.1002/cctc.202101292

Source DB:  PubMed          Journal:  ChemCatChem        ISSN: 1867-3880            Impact factor:   5.497


  122 in total

1.  Visible-Light-Promoted Asymmetric Cross-Dehydrogenative Coupling of Tertiary Amines to Ketones by Synergistic Multiple Catalysis.

Authors:  Qi Yang; Long Zhang; Chen Ye; Sanzhong Luo; Li-Zhu Wu; Chen-Ho Tung
Journal:  Angew Chem Int Ed Engl       Date:  2017-02-17       Impact factor: 15.336

2.  Enantioselective catalysis of photochemical reactions.

Authors:  Richard Brimioulle; Dominik Lenhart; Mark M Maturi; Thorsten Bach
Journal:  Angew Chem Int Ed Engl       Date:  2015-02-27       Impact factor: 15.336

3.  Stereoselective inhibition of the binding of [3H]PK 11195 to peripheral-type benzodiazepine binding sites by a quinolinepropanamide derivative.

Authors:  M C Dubroeucq; J Bénavidès; A Doble; F Guilloux; D Allam; N Vaucher; P Bertrand; C Guérémy; C Renault; A Uzan
Journal:  Eur J Pharmacol       Date:  1986-09-09       Impact factor: 4.432

4.  Organocatalytic Enantioselective Protonation for Photoreduction of Activated Ketones and Ketimines Induced by Visible Light.

Authors:  Lu Lin; Xiangbin Bai; Xinyi Ye; Xiaowei Zhao; Choon-Hong Tan; Zhiyong Jiang
Journal:  Angew Chem Int Ed Engl       Date:  2017-10-04       Impact factor: 15.336

5.  Porous Ru(bpy)32+-Linked Polymers for Recyclable Photocatalysis of Enantioselective Alkylation of Aldehydes.

Authors:  Yi Luo; Zi-Yue Xu; Hui Wang; Xing-Wen Sun; Zhan-Ting Li; Dan-Wei Zhang
Journal:  ACS Macro Lett       Date:  2020-01-02       Impact factor: 6.903

6.  Visible-Light-Enabled Enantioconvergent Synthesis of α-Amino Acid Derivatives via Synergistic Brønsted Acid/Photoredox Catalysis.

Authors:  Chao Che; Yi-Nan Li; Xiang Cheng; Yi-Nan Lu; Chun-Jiang Wang
Journal:  Angew Chem Int Ed Engl       Date:  2021-01-04       Impact factor: 15.336

7.  A chiral thioxanthone as an organocatalyst for enantioselective [2+2] photocycloaddition reactions induced by visible light.

Authors:  Rafael Alonso; Thorsten Bach
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-19       Impact factor: 15.336

8.  Light-driven deracemization enabled by excited-state electron transfer.

Authors:  Nick Y Shin; Jonathan M Ryss; Xin Zhang; Scott J Miller; Robert R Knowles
Journal:  Science       Date:  2019-10-18       Impact factor: 47.728

9.  Photochemical Stereocontrol Using Tandem Photoredox-Chiral Lewis Acid Catalysis.

Authors:  Tehshik P Yoon
Journal:  Acc Chem Res       Date:  2016-08-09       Impact factor: 22.384

10.  Light-Triggered Catalytic Asymmetric Allylic Benzylation with Photogenerated C-Nucleophiles.

Authors:  Suva Paria; Edoardo Carletti; Michela Marcon; Alessio Cherubini-Celli; Andrea Mazzanti; Marzio Rancan; Luca Dell'Amico; Marcella Bonchio; Xavier Companyó
Journal:  J Org Chem       Date:  2020-03-03       Impact factor: 4.354

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  1 in total

Review 1.  Strategies That Utilize Ion Pairing Interactions to Exert Selectivity Control in the Functionalization of C-H Bonds.

Authors:  James E Gillespie; Alexander Fanourakis; Robert J Phipps
Journal:  J Am Chem Soc       Date:  2022-09-30       Impact factor: 16.383

  1 in total

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