Literature DB >> 26000800

Bifunctional organocatalysts for the enantioselective synthesis of axially chiral isoquinoline N-oxides.

Ryota Miyaji1, Keisuke Asano1, Seijiro Matsubara1.   

Abstract

Bifunctional catalysts bearing amino and urea functional groups have been applied for a novel, highly enantioselective synthesis of axially chiral isoquinoline N-oxides, which are promising chiral ligands or organocatalysts in organic synthesis. This is the first example of highly enantioselective synthesis of axially chiral biaryls by bifunctional organocatalysts. Good-to-excellent enantioselectivities were obtained with a range of substrates.

Entities:  

Year:  2015        PMID: 26000800     DOI: 10.1021/jacs.5b04151

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  15 in total

1.  Asymmetric Synthesis of Gonytolide A: Strategic Use of an Aryl Halide Blocking Group for Oxidative Coupling.

Authors:  Xiaowei Wu; Takayuki Iwata; Adam Scharf; Tian Qin; Kyle D Reichl; John A Porco
Journal:  J Am Chem Soc       Date:  2018-04-25       Impact factor: 15.419

2.  Catalytic enantioselective synthesis of atropisomeric biaryls by a cation-directed O-alkylation.

Authors:  John D Jolliffe; Roly J Armstrong; Martin D Smith
Journal:  Nat Chem       Date:  2017-01-23       Impact factor: 24.427

3.  Organocatalytic asymmetric arylation of indoles enabled by azo groups.

Authors:  Liang-Wen Qi; Jian-Hui Mao; Jian Zhang; Bin Tan
Journal:  Nat Chem       Date:  2017-10-02       Impact factor: 24.427

Review 4.  Applications of Nonenzymatic Catalysts to the Alteration of Natural Products.

Authors:  Christopher R Shugrue; Scott J Miller
Journal:  Chem Rev       Date:  2017-06-05       Impact factor: 60.622

5.  Troponoid Atropisomerism: Studies on the Configurational Stability of Tropone-Amide Chiral Axes.

Authors:  Danielle R Hirsch; Anthony J Metrano; Elizabeth A Stone; Golo Storch; Scott J Miller; Ryan P Murelli
Journal:  Org Lett       Date:  2019-03-14       Impact factor: 6.005

6.  Enantioselective bromination of axially chiral cyanoarenes in the presence of bifunctional organocatalysts.

Authors:  Yuuki Wada; Akira Matsumoto; Keisuke Asano; Seijiro Matsubara
Journal:  RSC Adv       Date:  2019-10-04       Impact factor: 4.036

7.  Catalytic Dynamic Kinetic Resolutions in Tandem to Construct Two-Axis Terphenyl Atropisomers.

Authors:  Omar M Beleh; Edward Miller; F Dean Toste; Scott J Miller
Journal:  J Am Chem Soc       Date:  2020-09-14       Impact factor: 15.419

8.  Peptide-Catalyzed Fragment Couplings that Form Axially Chiral Non-C2 -Symmetric Biaryls.

Authors:  Gavin Coombs; Marcus H Sak; Scott J Miller
Journal:  Angew Chem Int Ed Engl       Date:  2019-12-30       Impact factor: 15.336

9.  Enantioselective synthesis of 3-arylquinazolin-4(3H)-ones via peptide-catalyzed atroposelective bromination.

Authors:  Matthew E Diener; Anthony J Metrano; Shuhei Kusano; Scott J Miller
Journal:  J Am Chem Soc       Date:  2015-09-18       Impact factor: 15.419

10.  Desymmetrization of Diarylmethylamido Bis(phenols) through Peptide-Catalyzed Bromination: Enantiodivergence as a Consequence of a 2 amu Alteration at an Achiral Residue within the Catalyst.

Authors:  Anna E Hurtley; Elizabeth A Stone; Anthony J Metrano; Scott J Miller
Journal:  J Org Chem       Date:  2017-11-03       Impact factor: 4.354

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