Literature DB >> 24294480

Photoredox Activation and Anion Binding Catalysis in the Dual Catalytic Enantioselective Synthesis of β-Amino Esters.

Giulia Bergonzini1, Corinna S Schindler, Carl-Johan Wallentin, Eric N Jacobsen, Corey R J Stephenson.   

Abstract

The enantioselective oxidative C-H functionalization of tetrahydroisoquinoline derivatives is achieved through the merger of photoredox and asymmetric anion-binding catalysis. This combination of two distinct catalysis concepts introduces a potentially general approach to asymmetric transformations in oxidative photocatalysis.

Entities:  

Year:  2014        PMID： 24294480      PMCID： PMC3842187          DOI： 10.1039/C3SC52265B

Source DB:  PubMed          Journal:  Chem Sci        ISSN： 2041-6520            Impact factor:   9.825


  62 in total

Review 1.  Recent advances in the catalytic asymmetric synthesis of beta-amino acids.

Authors:  Barbara Weiner; Wiktor Szymański; Dick B Janssen; Adriaan J Minnaard; Ben L Feringa
Journal:  Chem Soc Rev       Date:  2010-02-24       Impact factor: 54.564

Review 2.  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

3.  A cooperative hydrogen-bond-promoted organophotoredox catalysis strategy for highly diastereoselective, reductive enone cyclization.

Authors:  Matthias Neumann; Kirsten Zeitler
Journal:  Chemistry       Date:  2013-04-23       Impact factor: 5.236

4.  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

5.  Eosin Y catalyzed visible light oxidative C-C and C-P bond formation.

Authors:  Durga Prasad Hari; Burkhard König
Journal:  Org Lett       Date:  2011-07-11       Impact factor: 6.005

6.  CuBr-catalyzed direct indolation of tetrahydroisoquinolines via cross-dehydrogenative coupling between sp3 C-H and sp2 C-H bonds.

Authors:  Zhiping Li; Chao-Jun Li
Journal:  J Am Chem Soc       Date:  2005-05-18       Impact factor: 15.419

7.  Friedel-Crafts amidoalkylation via thermolysis and oxidative photocatalysis.

Authors:  Chunhui Dai; Francesco Meschini; Jagan M R Narayanam; Corey R J Stephenson
Journal:  J Org Chem       Date:  2012-04-18       Impact factor: 4.354

8.  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

9.  Beta-peptidic peptidomimetics.

Authors:  Dieter Seebach; James Gardiner
Journal:  Acc Chem Res       Date:  2008-06-26       Impact factor: 22.384

10.  Oxidative synthesis of alpha-amino nitriles from tertiary amines.

Authors:  Michael North
Journal:  Angew Chem Int Ed Engl       Date:  2004-08-13       Impact factor: 15.336
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  20 in total

1.  Asymmetric photoredox transition-metal catalysis activated by visible light.

Authors:  Haohua Huo; Xiaodong Shen; Chuanyong Wang; Lilu Zhang; Philipp Röse; Liang-An Chen; Klaus Harms; Michael Marsch; Gerhard Hilt; Eric Meggers
Journal:  Nature       Date:  2014-11-06       Impact factor: 49.962

2.  Enantioselective Intermolecular Radical C-H Amination.

Authors:  Li-Mei Jin; Pan Xu; Jingjing Xie; X Peter Zhang
Journal:  J Am Chem Soc       Date:  2020-11-25       Impact factor: 15.419

3.  B(C6F5)3-Catalyzed C-H Alkylation of N-Alkylamines Using Silicon Enolates without External Oxidant.

Authors:  Jessica Z Chan; Yejin Chang; Masayuki Wasa
Journal:  Org Lett       Date:  2019-01-29       Impact factor: 6.005

Review 4.  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

Review 5.  Visible Light-Induced Transition Metal Catalysis.

Authors:  Kelvin Pak Shing Cheung; Sumon Sarkar; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2021-10-08       Impact factor: 72.087

Review 6.  Photoredox-Catalyzed C-H Functionalization Reactions.

Authors:  Natalie Holmberg-Douglas; David A Nicewicz
Journal:  Chem Rev       Date:  2021-09-29       Impact factor: 60.622

7.  Amine Functionalization via Oxidative Photoredox Catalysis: Methodology Development and Complex Molecule Synthesis.

Authors:  Joel W Beatty; Corey R J Stephenson
Journal:  Acc Chem Res       Date:  2015-05-07       Impact factor: 22.384

8.  Regiodivergent synthesis of pyrazino-indolines vs. triazocines via α-imino carbenes addition to imidazolidines.

Authors:  Alejandro Guarnieri-Ibáñez; Adiran de Aguirre; Céline Besnard; Amalia I Poblador-Bahamonde; Jérôme Lacour
Journal:  Chem Sci       Date:  2020-11-23       Impact factor: 9.825

9.  A Case Study in Catalyst Generality: Simultaneous, Highly-Enantioselective Brønsted- and Lewis-Acid Mechanisms in Hydrogen-Bond-Donor Catalyzed Oxetane Openings.

Authors:  Daniel A Strassfeld; Russell F Algera; Zachary K Wickens; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2021-06-21       Impact factor: 16.383

10.  Controlling Enantioselectivity and Diastereoselectivity in Radical Cascade Cyclization for Construction of Bicyclic Structures.

Authors:  Congzhe Zhang; Duo-Sheng Wang; Wan-Chen Cindy Lee; Alexander M McKillop; X Peter Zhang
Journal:  J Am Chem Soc       Date:  2021-07-14       Impact factor: 16.383
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