Reversing Enantioselectivity Using Noncovalent Interactions in Asymmetric Dearomatization of β-Naphthols: The Power of 3,3′ Substituents in Chiral Phosphoric Acid Catalysts

2017 ◽  
Vol 19 (9) ◽  
pp. 2354-2357 ◽  
Author(s):  
Avtar Changotra ◽  
Sandip Das ◽  
Raghavan B. Sunoj
Keyword(s):  
Phosphoric Acid ◽  
Noncovalent Interactions ◽  
Acid Catalysts ◽  
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.

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

Enantioselective Intramolecular Allylic Substitution via Synergistic Palladium/Chiral Phosphoric Acid Catalysis: Insight into Stereoinduction through Statistical Modeling

2020 ◽  
Author(s):  
Cheng-Che Tsai ◽  
Christopher Sandford ◽  
Tao Wu ◽  
Buyun Chen ◽  
Matthew S. Sigman ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Statistical Modeling ◽  
Noncovalent Interactions ◽  
Linear Regression Analysis ◽  
Nonlinear Effects ◽  
Allylic Substitution ◽  
Phosphate Anion ◽  
Carbon Centers ◽  
Chiral Phosphoric Acid ◽  
Multivariable Linear Regression Analysis

The mode of asymmetric induction in an enantioselective intramolecular allylic substitution reaction catalyzed by a combination of palladium and a chiral phosphoric acid was investigated by a combined experimental and statistical modeling approach. Experiments to probe nonlinear effects, the reactivity of deuterium-labeled substrates, and control experiments revealed that the chiral phosphate anion is involved in stereoinduction. Using multivariable linear regression analysis, we identified that the presence of multiple noncovalent interactions with the chiral environment of the phosphate anion are integral to enantiocontrol in the transition state. The synthetic protocol to form chiral pyrrolidines was further applied to the asymmetric construction of C−O bonds at fully-substituted carbon centers in the synthesis of chiral 2,2-disubstituted benzomorpholines.

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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