Literature DB >> 25728854

Enantioselective catalysis of photochemical reactions.

Richard Brimioulle1, Dominik Lenhart, Mark M Maturi, Thorsten Bach.   

Abstract

The nature of the excited state renders the development of chiral catalysts for enantioselective photochemical reactions a considerable challenge. The absorption of a 400 nm photon corresponds to an energy uptake of approximately 300 kJ mol(-1) . Given the large distance to the ground state, innovative concepts are required to open reaction pathways that selectively lead to a single enantiomer of the desired product. This Review outlines the two major concepts of homogenously catalyzed enantioselective processes. The first part deals with chiral photocatalysts, which intervene in the photochemical key step and induce an asymmetric induction in this step. In the second part, reactions are presented in which the photochemical excitation is mediated by an achiral photocatalyst and the transfer of chirality is ensured by a second chiral catalyst (dual catalysis).
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords:  asymmetric catalysis; enantioselectivity; homogeneous catalysis; photocatalysis; photochemistry

Year:  2015        PMID: 25728854     DOI: 10.1002/anie.201411409

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  87 in total

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Authors:  Olga A Mukhina; Andrei G Kutateladze
Journal:  J Am Chem Soc       Date:  2016-02-16       Impact factor: 15.419

2.  Allenoates in Enantioselective [2+2] Cycloadditions: From a Mechanistic Curiosity to a Stereospecific Transformation.

Authors:  Johannes M Wiest; Michael L Conner; M Kevin Brown
Journal:  J Am Chem Soc       Date:  2018-11-05       Impact factor: 15.419

3.  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

4.  Asymmetric copper-catalyzed C-N cross-couplings induced by visible light.

Authors:  Quirin M Kainz; Carson D Matier; Agnieszka Bartoszewicz; Susan L Zultanski; Jonas C Peters; Gregory C Fu
Journal:  Science       Date:  2016-02-12       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.  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

7.  Enantioselective [2+2] Cycloadditions of Cinnamate Esters: Generalizing Lewis Acid Catalysis of Triplet Energy Transfer.

Authors:  Mary Elisabeth Daub; Hoimin Jung; Byung Joo Lee; Joonghee Won; Mu-Hyun Baik; Tehshik P Yoon
Journal:  J Am Chem Soc       Date:  2019-06-07       Impact factor: 15.419

8.  Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions.

Authors:  Saner Poplata; Andreas Tröster; You-Quan Zou; Thorsten Bach
Journal:  Chem Rev       Date:  2016-03-28       Impact factor: 60.622

9.  Visible-light excitation of iminium ions enables the enantioselective catalytic β-alkylation of enals.

Authors:  Mattia Silvi; Charlie Verrier; Yannick P Rey; Luca Buzzetti; Paolo Melchiorre
Journal:  Nat Chem       Date:  2017-03-20       Impact factor: 24.427

10.  Preparation of chiral-at-metal catalysts and their use in asymmetric photoredox chemistry.

Authors:  Jiajia Ma; Xiao Zhang; Xiaoqiang Huang; Shipeng Luo; Eric Meggers
Journal:  Nat Protoc       Date:  2018-03-01       Impact factor: 13.491

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