Literature DB >> 31489747

Asymmetric Synthesis of Heterocyclic γ-Amino-Acid and Diamine Derivatives by Three-Component Radical Cascade Reactions.

Danqing Zheng1, Armido Studer1.   

Abstract

An enantioselective three-component radical reaction of quinolines or pyridines with enamides and α-bromo carbonyl compounds by dual photoredox and chiral Brønsted acid catalysis is presented. A range of valuable chiral γ-amino-acid derivatives are accessible in high chemo-, regio-, and enantioselectivity from simple, readily available starting materials under mild reaction conditions. Using the same strategy, the asymmetric synthesis of 1,2-diamine derivatives is also reported.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Brønsted acids; amino acids; asymmetric synthesis; photochemistry; radicals

Year:  2019        PMID: 31489747     DOI: 10.1002/anie.201908987

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


  12 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

Review 2.  Recent Advances in 1,2-Amino(hetero)arylation of Alkenes.

Authors:  Yungeun Kwon; Qiu Wang
Journal:  Chem Asian J       Date:  2022-05-03

3.  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

4.  Asymmetric three-component olefin dicarbofunctionalization enabled by photoredox and copper dual catalysis.

Authors:  Peng-Zi Wang; Yuan Gao; Jun Chen; Xiao-Die Huan; Wen-Jing Xiao; Jia-Rong Chen
Journal:  Nat Commun       Date:  2021-03-22       Impact factor: 14.919

5.  Metal-free, visible-light induced enantioselective three-component dicarbofunctionalization and oxytrifluoromethylation of enamines via chiral phosphoric acid catalysis.

Authors:  Hui Liang; Dong-Sheng Ji; Guo-Qiang Xu; Yong-Chun Luo; Haixue Zheng; Peng-Fei Xu
Journal:  Chem Sci       Date:  2022-01-04       Impact factor: 9.825

6.  Unexpected ortho C-H bond activation in coordinated 7,8-benzoquinoline: synthesis and characterisation of heteroleptic Ir(iii)-7,8-benzoquinoline complexes.

Authors:  Kahnu Charan Pradhan; Hemanta K Kisan; Satyanarayan Pal
Journal:  RSC Adv       Date:  2021-03-30       Impact factor: 3.361

7.  Three-component 1,2-carboamination of vinyl boronic esters via amidyl radical induced 1,2-migration.

Authors:  Cai You; Armido Studer
Journal:  Chem Sci       Date:  2021-11-16       Impact factor: 9.825

8.  Allylboronic Esters as Acceptors in Radical Addition, Boron 1,2-Migration, and Trapping Cascades.

Authors:  Kalipada Jana; Armido Studer
Journal:  Org Lett       Date:  2022-01-26       Impact factor: 6.005

9.  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

Review 10.  Radical-Based Synthesis and Modification of Amino Acids.

Authors:  Francisco José Aguilar Troyano; Kay Merkens; Khadijah Anwar; Adrián Gómez-Suárez
Journal:  Angew Chem Int Ed Engl       Date:  2020-11-04       Impact factor: 15.336

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