Visible‐Light‐Enabled Enantioconvergent Synthesis of α‐Amino Acid Derivatives via Synergistic Brønsted Acid/Photoredox Catalysis

2021 ◽  
Author(s):  
Chao Che ◽  
Yi‐Nan Li ◽  
Xiang Cheng ◽  
Yi‐Nan Lu ◽  
Chun‐Jiang Wang
Keyword(s):  
Amino Acid ◽  
Visible Light ◽  
Amino Acid Derivatives ◽  
Bronsted Acid ◽  
Photoredox Catalysis ◽  
Brønsted Acid ◽  
Brönsted Acid

scholarly journals Organocatalytic Synthesis of α,α–Diaryl Substituted α–Amino Acid Derivatives by an Interrupted Three-Component Ugi Reaction

2019 ◽  
Vol 92 (2) ◽  
pp. 203-209 ◽  
Author(s):  
Danijel Glavač ◽  
Ivanka Jerić ◽  
Matija Gredičak
Keyword(s):  
Reaction Mechanism ◽  
Amino Acid ◽  
Ugi Reaction ◽  
Amino Acid Derivatives ◽  
Acid Catalysts ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Brönsted Acid ◽  
Bronsted Acid Catalysts

An organocatalytic interrupted three-component Ugi reaction for the synthesis of α,α–diaryl α–amino acid derivatives is described. The transformation proceeds with a range of isocyanides and 3-aryl isoindolinone alcohols using Brønsted acid catalysts to afford products in good to excellent yields. Based on the obtained results, a reaction mechanism is proposed and discussed.

Auto-oxidation promoted sp3 C–H arylation of glycine derivatives

2018 ◽  
Vol 16 (27) ◽  
pp. 4985-4989 ◽  
Author(s):  
Yuanyuan Wei ◽  
Jie Wang ◽  
Yajun Wang ◽  
Xiaoqiang Yao ◽  
Caixia Yang ◽  
...  
Keyword(s):  
Amino Acid ◽  
Environmentally Benign ◽  
Amino Acid Derivatives ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Reaction Conditions ◽  
Brönsted Acid ◽  
Reaction Proceeds ◽  
Glycine Derivatives

An auto-oxidation promoted sp3 C–H arylation reaction between N-aryl glycine derivatives and electron-rich arenes, leading to the formation of N-aryl α-aryl α-amino acid derivatives, is described. This atom-economical and environmentally benign reaction proceeds smoothly under mild reaction conditions and requires only Brønsted acid and oxygen (balloon). A plausible radical involved mechanism is proposed.

scholarly journals Brønsted Acid-Catalyzed Epimerization-Free Preparation of Dual-Protected Amino Acid Derivatives

ACS Omega ◽  
2017 ◽  
Vol 2 (6) ◽  
pp. 2967-2976 ◽  
Author(s):  
Pedro P. de Castro ◽  
Isabela M. R. Rimulo ◽  
Angelina M. de Almeida ◽  
Renata Diniz ◽  
Giovanni W. Amarante
Keyword(s):  
Amino Acid ◽  
Amino Acid Derivatives ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Protected Amino Acid ◽  
Brönsted Acid ◽  
Acid Catalyzed

An uncommon use of irradiated flavins: Brønsted acid catalysis

2020 ◽  
Vol 56 (42) ◽  
pp. 5661-5664
Author(s):  
Yukihiro Arakawa ◽  
Tomohiro Mihara ◽  
Hiroki Fujii ◽  
Keiji Minagawa ◽  
Yasushi Imada
Keyword(s):  
Visible Light ◽  
Visible Light Irradiation ◽  
Acid Catalysis ◽  
Light Irradiation ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Mild Conditions ◽  
Brönsted Acid ◽  
Bronsted Acid Catalysis

Visible light irradiation to flavins in the presence of thiols and O2 provides Brønsted acidic species that can be used as efficient catalysts for thioacetalizations and for Mannich-type reactions under non-irradiation and mild conditions.

Brønsted acid cocatalysis in photocatalytic intramolecular coupling of tertiary amines: efficient synthesis of 2-arylindols

2016 ◽  
Vol 14 (31) ◽  
pp. 7447-7450 ◽  
Author(s):  
Xiaoqian Yuan ◽  
Xinxin Wu ◽  
Shupeng Dong ◽  
Guibing Wu ◽  
Jinxing Ye
Keyword(s):  
Visible Light ◽  
Visible Light Irradiation ◽  
Room Temperature ◽  
Coupling Reaction ◽  
Bronsted Acid ◽  
Tertiary Amines ◽  
Brønsted Acid ◽  
Efficient Synthesis ◽  
Unsaturated Ketones ◽  
Brönsted Acid

We report herein a highly efficient intramolecular coupling reaction of tertiary amines and ketones (α,β-unsaturated ketones) by using a Brønsted acid as a cocatalyst, affording 2-arylindols in good to excellent yields (up to 92%) under visible light irradiation at room temperature.

scholarly journals Chiral phosphine-mediated intramolecular [3 + 2] annulation: enhanced enantioselectivity by achiral Brønsted acid

2017 ◽  
Vol 8 (7) ◽  
pp. 5196-5200 ◽  
Author(s):  
Weijun Yao ◽  
Zhaoyuan Yu ◽  
Shan Wen ◽  
Huanzhen Ni ◽  
Nisar Ullah ◽  
...  
Keyword(s):  
Amino Acid ◽  
Bronsted Acids ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Brönsted Acid

Enantioselective intramolecular [3 + 2] annulation of chalcone–allenes catalyzed by amino acid-derived phosphines and achiral Brønsted acids has been developed.

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