Literature DB >> 30256118

Organocatalytic Enantioselective Addition of α-Aminoalkyl Radicals to Isoquinolines.

Xiangyuan Liu1, Yang Liu1, Guobi Chai2, Baokun Qiao1, Xiaowei Zhao1, Zhiyong Jiang1,3.   

Abstract

With a dual organocatalytic system involving a chiral phosphoric acid and a dicyanopyrazine-derived chromophore (DPZ) photosensitizer and under the irradiation with visible light, an enantioselective Minisci-type addition of α-amino acid-derived redox-active esters (RAEs) to isoquinolines has been developed. A variety of prochiral α-aminoalkyl radicals generated from RAEs were successfully introduced on isoquinolines, providing a range of valuable α-isoquinoline-substituted chiral secondary amines in high yields with good to excellent enantioselectivities.

Entities:  

Year:  2018        PMID: 30256118     DOI: 10.1021/acs.orglett.8b02791

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  8 in total

1.  Advancements in Visible-Light-Enabled Radical C(sp)2-H Alkylation of (Hetero)arenes.

Authors:  Alexandra C Sun; Rory C McAtee; Edward J McClain; Corey R J Stephenson
Journal:  Synthesis (Stuttg)       Date:  2019-01-25       Impact factor: 2.969

2.  Asymmetric Photocatalysis Enabled by Chiral Organocatalysts.

Authors:  Wang Yao; Emmanuel A Bazan Bergamino; Ming-Yu Ngai
Journal:  ChemCatChem       Date:  2021-10-21       Impact factor: 5.497

Review 3.  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 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

5.  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

6.  Hydrogen Atom Transfer Driven Enantioselective Minisci Reaction of Alcohols.

Authors:  Avene C Colgan; Rupert S J Proctor; David C Gibson; Padon Chuentragool; Antti S K Lahdenperä; Kristaps Ermanis; Robert J Phipps
Journal:  Angew Chem Int Ed Engl       Date:  2022-04-27       Impact factor: 16.823

7.  Phosphite mediated asymmetric N to C migration for the synthesis of chiral heterocycles from primary amines.

Authors:  Soniya Rani; Soumya Ranjan Dash; Asish Bera; Md Nirshad Alam; Kumar Vanka; Pradip Maity
Journal:  Chem Sci       Date:  2021-05-28       Impact factor: 9.825

8.  Predictive Multivariate Linear Regression Analysis Guides Successful Catalytic Enantioselective Minisci Reactions of Diazines.

Authors:  Jolene P Reid; Rupert S J Proctor; Matthew S Sigman; Robert J Phipps
Journal:  J Am Chem Soc       Date:  2019-11-21       Impact factor: 15.419

  8 in total

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