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.

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.

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...

Chiral phosphoric acid catalyzed enantioselective annulation of acyclic enecarbamates to in situ-generated ortho-quinone methides

2017 ◽  
Vol 15 (35) ◽  
pp. 7272-7276 ◽  
Author(s):  
Chandan Gharui ◽  
Shreya Singh ◽  
Subhas Chandra Pan
Keyword(s):  
Phosphoric Acid ◽  
Cycloaddition Reaction ◽  
Quinone Methides ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed ◽  
Phosphoric Acids

The first organocatalytic asymmetric [4 + 2]-cycloaddition reaction between acyclic enecarbamates with in situ generated ortho-quinone methides has been developed using chiral phosphoric acids as catalysts.

Lewis acid-catalyzed tandem cyclization of in situ generated o-quinone methides and arylsulfonyl hydrazides for a one-pot entry to 3-sulfonylbenzofurans

2019 ◽  
Vol 6 (24) ◽  
pp. 3929-3933 ◽  
Author(s):  
Fan-Xiao Meng ◽  
Ruo-Nan Wang ◽  
Hong-Li Huang ◽  
Shu-Wen Gong ◽  
Qian-Li Li ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Quinone Methides ◽  
One Pot ◽  
Acid Catalyzed ◽  
Tandem Cyclization ◽  
First Time

Lewis acid-mediated one-pot tandem cyclization of o-QMs with arylsulfonyl hydrazides was described for the first time and the corresponding 3-sulfonylbenzofuran products were obtained in moderate to good yields.

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.

Asymmetric organocatalytic synthesis of chiral 3,3-disubstituted oxindolesviaa 1,6-conjugate addition reaction

2018 ◽  
Vol 16 (29) ◽  
pp. 5301-5309 ◽  
Author(s):  
Abdul Rahman ◽  
Qiaoxia Zhou ◽  
Xufeng Lin
Keyword(s):  
Phosphoric Acid ◽  
Addition Reaction ◽  
Conjugate Addition ◽  
Quinone Methides ◽  
Acid Catalyzed

The chiral spirocyclic phosphoric acid-catalyzed enantioselective 1,6-conjugate addition reaction ofpara-quinone methides derived fromN-unprotected isatins with indoles was developed.

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
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