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.

scholarly journals Chiral Brønsted acid-catalyzed enantioselective Friedel–Crafts reaction of 2-methoxyfuran with aliphatic ketimines generated in situ

2016 ◽  
Vol 7 (2) ◽  
pp. 1057-1062 ◽  
Author(s):  
Azusa Kondoh ◽  
Yusuke Ota ◽  
Takazumi Komuro ◽  
Fuyuki Egawa ◽  
Kyohei Kanomata ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Acid Catalyst ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Chiral Phosphoric Acid ◽  
Brönsted Acid ◽  
Acid Catalyzed ◽  
Chiral Bronsted Acid

An enantioselective Friedel–Crafts reaction with aliphatic ketimines generated in situ from hemiaminal ethers afforded products with high enantioselectivity under the influence of a chiral phosphoric acid catalyst.

scholarly journals Synthesis of six-membered spirooxindolesviaa chiral Brønsted acid-catalyzed asymmetric intramolecular Friedel–Crafts reaction

RSC Advances ◽  
2018 ◽  
Vol 8 (65) ◽  
pp. 37035-37039 ◽  
Author(s):  
Hui-Xuan Chen ◽  
Yaqi Zhang ◽  
Yuyang Zhang ◽  
Xuefeng He ◽  
Zhen-Wei Zhang ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Chiral Phosphoric Acid ◽  
Brönsted Acid ◽  
Acid Catalyzed ◽  
Chiral Bronsted Acid

A chiral phosphoric acid-catalyzed asymmetric intramolecular Friedel–Crafts reaction for the synthesis of 3′,4′-dihydro-2′H-spiro[indoline-3,1′-pyrrolo[1,2-a]pyrazin]-2-ones.

scholarly journals Chiral Brønsted acid-catalyzed Friedel–Crafts alkylation of electron-rich arenes with in situ-generated ortho-quinone methides: highly enantioselective synthesis of diarylindolylmethanes and triarylmethanes

2015 ◽  
Vol 51 (8) ◽  
pp. 1461-1464 ◽  
Author(s):  
Satyajit Saha ◽  
Santosh Kumar Alamsetti ◽  
Christoph Schneider
Keyword(s):  
Enantioselective Synthesis ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Quinone Methides ◽  
Reaction Conditions ◽  
Brönsted Acid ◽  
Acid Catalyzed ◽  
Chiral Bronsted Acid ◽  
Hydrogen Bonded

Hydrogen-bonded, in situ-generated ortho-quinone methides undergo highly enantioselective Friedel–Crafts reactions with indoles and naphthols under mild reaction conditions.

Chiral phosphoric acid-catalyzed direct asymmetric mannich reaction of cyclicC-acylimines with simple ketones: facile access to C2-quaternary indolin-3-ones

2018 ◽  
Vol 54 (66) ◽  
pp. 9151-9154 ◽  
Author(s):  
Jin-Shan Li ◽  
Yong-Jie Liu ◽  
Shen Li ◽  
Jun-An Ma
Keyword(s):  
Phosphoric Acid ◽  
Mannich Reaction ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Chiral Phosphoric Acid ◽  
Brönsted Acid ◽  
Acid Catalyzed ◽  
Chiral Bronsted Acid

A chiral Brønsted acid-catalyzed direct asymmetric Mannich reaction of simple ketones with cyclicC-acylimines has been established for the synthesis of C2-quaternary indolin-3-ones.

Chiral Brønsted acid-catalyzed hydrophosphonylation of imines—DFT study on the effect of substituents of phosphoric acid

Tetrahedron ◽  
2009 ◽  
Vol 65 (26) ◽  
pp. 4950-4956 ◽  
Author(s):  
Takahiko Akiyama ◽  
Hisashi Morita ◽  
Prabhakar Bachu ◽  
Keiji Mori ◽  
Masahiro Yamanaka ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Dft Study ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Effect Of Substituents ◽  
Brönsted Acid ◽  
Acid Catalyzed ◽  
Chiral Bronsted Acid

Chiral Brønsted Acid from Chiral Phosphoric Acid Boron Complex and Water: Asymmetric Reduction of Indoles

2020 ◽  
Vol 132 (8) ◽  
pp. 3320-3325 ◽  
Author(s):  
Kai Yang ◽  
Yixian Lou ◽  
Chenglan Wang ◽  
Liang‐Wen Qi ◽  
Tongchang Fang ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Asymmetric Reduction ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Chiral Phosphoric Acid ◽  
Brönsted Acid ◽  
Boron Complex ◽  
Chiral Bronsted Acid

Chiral phosphoric acid catalyzed enantioselective N-alkylation of indoles with in situ generated cyclic N-acyl ketimines

2018 ◽  
Vol 54 (66) ◽  
pp. 9230-9233 ◽  
Author(s):  
Lvye Zhang ◽  
Binqiang Wu ◽  
Zhangtao Chen ◽  
Jinjin Hu ◽  
Xiaofei Zeng ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Alkylation Reaction ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed

A chiral SPINOL derived phosphoric acid-catalyzed asymmetric N-alkylation reaction of indoles with cyclic α-diaryl-substituted N-acyl imines, which are generated in situ from 3-aryl 3-hydroxyisoindo-linones, has been demonstrated.

Chiral Brønsted Acid-Catalyzed Stereoselective Mannich-Type Reaction of Azlactones with Aldimines

2014 ◽  
Vol 80 (1) ◽  
pp. 590-594 ◽  
Author(s):  
Eloah P. Ávila ◽  
Rodrigo M. S. Justo ◽  
Vanessa P. Gonçalves ◽  
Adriane A. Pereira ◽  
Renata Diniz ◽  
...  
Keyword(s):  
Bronsted Acid ◽  
Brønsted Acid ◽  
Type Reaction ◽  
Brönsted Acid ◽  
Acid Catalyzed ◽  
Chiral Bronsted Acid

Chiral phosphoric acid catalyzed enantioselective addition of thiols to in situ generated ketimines: Synthesis of N , S -ketals

2017 ◽  
Vol 58 (2) ◽  
pp. 145-151 ◽  
Author(s):  
Rajshekhar A. Unhale ◽  
Nagaraju Molleti ◽  
Nirmal K. Rana ◽  
Sivasankaran Dhanasekaran ◽  
Subhrajyoti Bhandary ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed ◽  
Enantioselective Addition

scholarly journals An asymmetric Brønsted acid-catalyzed Friedel–Crafts reaction of indoles with cyclic N-sulfimines

RSC Advances ◽  
2017 ◽  
Vol 7 (54) ◽  
pp. 34283-34286 ◽  
Author(s):  
Sang Gyu Lee ◽  
Sung-Gon Kim
Keyword(s):  
Phosphoric Acid ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Chiral Phosphoric Acid ◽  
Brönsted Acid ◽  
Acid Catalyzed

A highly enantioselective organocatalytic Friedel–Crafts reaction of indoles with cyclic N-sulfimines using a chiral phosphoric acid as an organocatalyst has been developed.

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