Asymmetric Cycloaddition of ortho-Hydroxyphenyl-Substituted para-Quinone Methides and Enamides Catalyzed by Chiral Phosphoric Acid

2019 ◽  
Vol 84 (12) ◽  
pp. 7883-7893 ◽  
Author(s):  
Guo-Hui Yang ◽  
Qun Zhao ◽  
Zhi-Pei Zhang ◽  
Han-Liang Zheng ◽  
Li Chen ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Quinone Methides ◽  
Chiral Phosphoric Acid

scholarly journals Organocatalytic Asymmetric [2 + 4] Cycloadditions of 3-Vinylindoles with ortho-Quinone Methides

Molecules ◽  
2021 ◽  
Vol 26 (21) ◽  
pp. 6751
Author(s):  
Si-Jia Liu ◽  
Man-Su Tu ◽  
Kai-Yue Liu ◽  
Jia-Yi Chen ◽  
Shao-Fei Ni ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Structural Diversity ◽  
Quinone Methides ◽  
Chiral Phosphoric Acid ◽  
Catalytic Asymmetric ◽  
High Yields ◽  
Asymmetric Cycloadditions

Catalytic asymmetric [2 + 4] cycloadditions of 3-vinylindoles with ortho-quinone methides and their precursors were carried out in the presence of chiral phosphoric acid to afford a series of indole-containing chroman derivatives with structural diversity in overall high yields (up to 98%), good diastereoselectivities (up to 93:7 dr) and moderate to excellent enantioselectivities (up to 98% ee). This approach not only enriches the chemistry of catalytic asymmetric cycloadditions involving 3-vinylindoles but is also useful for synthesizing chiral chroman derivatives.

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 Organocatalytic enantioselective conjugate addition of 2-naphthols to ortho-hydroxyphenyl substituted para-quinone methides: access to unsymmetrical triarylmethanes

RSC Advances ◽  
2019 ◽  
Vol 9 (42) ◽  
pp. 24212-24217 ◽  
Author(s):  
Yuyu Cheng ◽  
Zhiqiang Fang ◽  
Yanwen Jia ◽  
Zhongyue Lu ◽  
Wenjun Li ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Conjugate Addition ◽  
Quinone Methides ◽  
Chiral Phosphoric Acid

The enantioselective conjugate addition of 2-naphthols to ortho-hydroxyphenyl substituted para-quinone methides has been achieved with the aid of a chiral phosphoric acid.

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.

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 A Molecular Stereostructure Descriptor Based On Spherical Projection

Synlett ◽  
2020 ◽  
Author(s):  
Shuo-Qing Zhang ◽  
Xin Hong ◽  
Li-Cheng Xu ◽  
Xin Li ◽  
Miao-Jiong Tang ◽  
...  
Keyword(s):  
Machine Learning ◽  
Phosphoric Acid ◽  
Asymmetric Catalysis ◽  
Van Der Waals ◽  
Chiral Phosphoric Acid ◽  
Key Features ◽  
Precise Representation ◽  
Spherical Projection

AbstractDescription of molecular stereostructure is critical for the machine learning prediction of asymmetric catalysis. Herein we report a spherical projection descriptor of molecular stereostructure (SPMS), which allows precise representation of the molecular van der Waals (vdW) surface. The key features of SPMS descriptor are presented using the examples of chiral phosphoric acid, and the machine learning application is demonstrated in Denmark’s dataset of asymmetric thiol addition to N-acylimines. In addition, SPMS descriptor also offers a color-coded diagram that provides straightforward chemical interpretation of the steric environment.

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