Organocatalytic Stereoselective 1,6-Addition of Thiolacetic Acids to Propargylic Indole Imine Methides: Access to Axially Chiral Sulfur-containing Tetrasubstituted Allenes

2021 ◽  
Author(s):  
Ziyang Wang ◽  
Xiao Lin ◽  
Xuling Chen ◽  
Pengfei Li ◽  
Wenjun Li
Keyword(s):  
Phosphoric Acid ◽  
Conjugate Addition ◽  
Chiral Phosphoric Acid ◽  
Axially Chiral ◽  
Propargylic Alcohol ◽  
Acid Catalyzed ◽  
Sulfur Containing ◽  
Thiolacetic Acid

A chiral phosphoric acid catalyzed enantioselective 1,6-conjugate addition of thiolacetic acid to propargylic indole imine methide in situ formed from α-(3-indolyl) propargylic alcohol has been established, which enables the formation...

Organocatalytic site- and stereoselective 1,6-additions of N-aryl-3-oxobutanamides to propargylic aza-p-quinone methides

2020 ◽  
Vol 7 (21) ◽  
pp. 3446-3451
Author(s):  
Fushuai Li ◽  
Xuling Chen ◽  
Shuai Liang ◽  
Zhenyan Shi ◽  
Pengfei Li ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Conjugate Addition ◽  
Quinone Methides ◽  
Propargylic Alcohols ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed ◽  
Site Selective ◽  
First Time

A chiral phosphoric acid catalyzed site-selective 1,6-conjugate addition of N-aryl-3-oxobutanamides to in situ formed propargylic aza-p-quinone methides from propargylic alcohols has been established for the first time.

scholarly journals Recent advances in the asymmetric phosphoric acid-catalyzed synthesis of axially chiral compounds

2021 ◽  
Vol 17 ◽  
pp. 2729-2764
Author(s):  
Alemayehu Gashaw Woldegiorgis ◽  
Xufeng Lin
Keyword(s):  
Phosphoric Acid ◽  
Asymmetric Catalysis ◽  
Medicinal Chemistry ◽  
High Efficiency ◽  
Biologically Active ◽  
Chiral Compounds ◽  
Chiral Phosphoric Acid ◽  
Wide Range ◽  
Axially Chiral ◽  
Acid Catalyzed

In recent years, the synthesis of axially chiral compounds has received considerable attention due to their extensive application as biologically active compounds in medicinal chemistry and as chiral ligands in asymmetric catalysis. Chiral phosphoric acids are recognized as efficient organocatalysts for a variety of enantioselective transformations. In this review, we summarize the recent development of chiral phosphoric acid-catalyzed synthesis of a wide range of axially chiral biaryls, heterobiaryls, vinylarenes, N-arylamines, spiranes, and allenes with high efficiency and excellent stereoselectivity.

Chiral phosphoric acid catalyzed atroposelective and diastereoselective synthesis of 9-aryltetrahydroacridines

2020 ◽  
Vol 7 (16) ◽  
pp. 2255-2262 ◽  
Author(s):  
You-Dong Shao ◽  
Dan-Dan Han ◽  
Wen-Yue Ma ◽  
Dao-Juan Cheng
Keyword(s):  
Phosphoric Acid ◽  
Diastereoselective Synthesis ◽  
Chiral Phosphoric Acid ◽  
Axially Chiral ◽  
Acid Catalyzed

A chiral phosphoric acid catalyzed atroposelective annulation between 2-aminoaryl ketones and alicyclic ketones has been developed to access a new library of enantioenriched axially chiral 9-aryltetrahydroacridines.

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.

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 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

Chiral phosphoric acid catalyzed asymmetric addition of naphthols to para-quinone methides

2016 ◽  
Vol 14 (24) ◽  
pp. 5751-5754 ◽  
Author(s):  
Yuk Fai Wong ◽  
Zhaobin Wang ◽  
Jianwei Sun
Keyword(s):  
Phosphoric Acid ◽  
Quinone Methides ◽  
Asymmetric Addition ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed

An asymmetric addition of naphthols to in situ generated para-quinone methides catalyzed by a chiral phosphoric acid is described.

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.

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