Enantioselective Activation of Aldehydes by Chiral Phosphoric Acid Catalysts in an Aza-ene-type Reaction between Glyoxylate and Enecarbamate

2008 ◽  
Vol 47 (22) ◽  
pp. 4122-4125 ◽  
Author(s):  
Masahiro Terada ◽  
Kazuyo Soga ◽  
Norie Momiyama
Keyword(s):  
Phosphoric Acid ◽  
Acid Catalysts ◽  
Type Reaction ◽  
Chiral Phosphoric Acid

scholarly journals QM/MM study on the enantioselectivity of spiroacetalization catalysed by an imidodiphosphoric acid catalyst: how confinement works

2016 ◽  
Vol 14 (11) ◽  
pp. 3031-3039 ◽  
Author(s):  
Luis Simón ◽  
Robert S. Paton
Keyword(s):  
Phosphoric Acid ◽  
Acid Catalyst ◽  
Acid Catalysts ◽  
Chiral Phosphoric Acid

An explanation of why confined imidodiphosphoric acid catalyst succeeds where other chiral phosphoric acid catalysts fail.

Asymmetric C-H and N-H functionalization of Indoles involving Central Chirality via Chiral Phosphoric Acid Catalysis

2021 ◽  
Vol 18 ◽  
Author(s):  
Alemayehu Gashaw ◽  
Dereje Kebebew Debeli ◽  
Meseret Chemeda
Keyword(s):  
Phosphoric Acid ◽  
Organic Compounds ◽  
Organic Synthesis ◽  
Acid Catalysis ◽  
Bond Formation ◽  
Acid Catalysts ◽  
Asymmetric Syntheses ◽  
Chiral Phosphoric Acid ◽  
Great Progress ◽  
Interesting Area

: The C-H and N-H functionalization of indoles is an interesting area of research that has a useful impact on organic synthesis due to the availability of chiral indole scaffolds in the discovery of drugs, synthetic bioactive compounds, and natural products. The chiral phosphoric acid catalysts (CPAs) have proven to be a powerful and versatile class of enantioselective organocatalysts. Many asymmetric syntheses of organic compounds have been carried out with these catalysts in C–C and C-N bond formation reactions, and great progress has been reported. By 2011, several reviews were published covering some important topics and recent achievements in this field. Therefore, in this review, the most recent advances, research breakthroughs with key examples involving mechanisms of CPA-catalyzed C-H and N-H functionalization of indoles to form central chirality via Friedel Crafts, Michael type, and rearrangement reactions were reviewed and reported.

Organocatalytic asymmetric synthesis of benzazepinoindole derivatives with trifluoromethylated quaternary stereocenters by chiral phosphoric acid catalysts

2018 ◽  
Vol 16 (8) ◽  
pp. 1367-1374 ◽  
Author(s):  
Abdul Rahman ◽  
En Xie ◽  
Xufeng Lin
Keyword(s):  
Phosphoric Acid ◽  
Asymmetric Synthesis ◽  
Acid Catalysts ◽  
Chiral Phosphoric Acid ◽  
Quaternary Stereocenters

An enantioselective aza-Friedel–Crafts reaction of trifluoromethyl dihydrobenzoazepinoindoles with pyrroles or indoles catalyzed by a chiral spirocyclic phosphoric acid was developed.

A chiral Brønsted acid-catalyzed highly enantioselective Mannich-type reaction of α-diazo esters with in situ generated N-acyl ketimines

2018 ◽  
Vol 54 (28) ◽  
pp. 3516-3519 ◽  
Author(s):  
Rajshekhar A. Unhale ◽  
Milon M. Sadhu ◽  
Sumit K. Ray ◽  
Rayhan G. Biswas ◽  
Vinod K. Singh
Keyword(s):  
Phosphoric Acid ◽  
Reaction Conditions ◽  
Type Reaction ◽  
Chiral Phosphoric Acid ◽  
Brönsted Acid ◽  
Diazo Esters ◽  
Reaction Proceeds ◽  
Acid Catalyzed ◽  
Chiral Bronsted Acid

A chiral phosphoric acid-catalyzed asymmetric Mannich-type reaction of α-diazo esters with in situ generated N-acyl ketimines, derived from 3-aryl-3-hydroxyisoindolinones has been demonstrated. The reaction proceeds smoothly under mild reaction conditions.

Design and synthesis of new alkyl‐based chiral phosphoric acid catalysts

Chirality ◽  
2019 ◽  
Vol 31 (8) ◽  
pp. 592-602
Author(s):  
Xiaoxue Tang ◽  
Hualing He ◽  
Xiantao Fang ◽  
Zexu Chang ◽  
Jon C. Antilla
Keyword(s):  
Phosphoric Acid ◽  
Acid Catalysts ◽  
Design And Synthesis ◽  
Chiral Phosphoric Acid

Asymmetric Cycloetherification via the Kinetic Resolution of Alcohols Using Chiral Phosphoric Acid Catalysts

2016 ◽  
Vol 45 (11) ◽  
pp. 1300-1303 ◽  
Author(s):  
Naoki Yoneda ◽  
Akira Matsumoto ◽  
Keisuke Asano ◽  
Seijiro Matsubara
Keyword(s):  
Phosphoric Acid ◽  
Kinetic Resolution ◽  
Acid Catalysts ◽  
Chiral Phosphoric Acid

Chemoselective N–H functionalization of indole derivatives via the Reissert-type reaction catalyzed by a chiral phosphoric acid

2018 ◽  
Vol 16 (33) ◽  
pp. 6146-6154 ◽  
Author(s):  
Yue Cai ◽  
Qing Gu ◽  
Shu-Li You
Keyword(s):  
Phosphoric Acid ◽  
Indole Derivatives ◽  
Type Reaction ◽  
Chiral Phosphoric Acid

An asymmetric N-alkylation of indole derivatives via the Reissert-type reaction was realized in the presence of 10 mol% chiral phosphoric acid.

Enantioselective Synthesis of anti-1,2-Oxaborinan-3-enes from Aldehydes and 1,1-Di(boryl)alk-3-enes Using Ruthenium and Chiral Phosphoric Acid Catalysts

2017 ◽  
Vol 139 (31) ◽  
pp. 10903-10908 ◽  
Author(s):  
Tomoya Miura ◽  
Junki Nakahashi ◽  
Wang Zhou ◽  
Yota Shiratori ◽  
Scott G. Stewart ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Enantioselective Synthesis ◽  
Acid Catalysts ◽  
Chiral Phosphoric Acid
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