On the Question of Steric Repulsion versus Noncovalent Attractive Interactions in Chiral Phosphoric Acid Catalyzed Asymmetric Reactions

2021 ◽  
Author(s):  
Soumi Tribedi ◽  
Kazuo Kitaura ◽  
Takahito Nakajima ◽  
Raghavan B. Sunoj
Keyword(s):  
Phosphoric Acid ◽  
Asymmetric Catalysis ◽  
Transition States ◽  
Asymmetric Reactions ◽  
Steric Interaction ◽  
Steric Repulsion ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed

The origin of enantioselectivity in asymmetric catalysis is often built around the differential steric interaction in the enantiocontrolling transition states (TSs). Closer perusal of enantiocontrolling TSs in an increasingly diverse...

scholarly journals Catalytic Enantioselective Synthesis of 4-Amino-1,2,3,4-tetrahydropyridine Derivatives from Intramolecular Nucleophilic Addition Reaction of Tertiary Enamides

Synlett ◽  
2018 ◽  
Vol 30 (04) ◽  
pp. 483-487 ◽  
Author(s):  
Shuo Tong ◽  
Mei-Xiang Wang
Keyword(s):  
Phosphoric Acid ◽  
Asymmetric Catalysis ◽  
Nucleophilic Addition ◽  
Addition Reaction ◽  
Enantioselective Synthesis ◽  
Chiral Phosphoric Acid ◽  
Substrate Engineering ◽  
Nucleophilic Addition Reaction ◽  
Engineering Strategy ◽  
Acid Catalyzed

A general and efficient method for the synthesis of highly enantiopure 4-amino-1,2,3,4-tetradydropyridine derivatives based on chiral phosphoric acid catalyzed intramolecular nucleophilic addition of tertiary enamides to imines has been developed. We have also demonstrated a substrate engineering strategy to significantly improve the enantioselectivity of asymmetric catalysis

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.

Enantioselective construction of a 2,2′-bisindolylmethane scaffold via catalytic asymmetric reactions of 2-indolylmethanols with 3-alkylindoles

2015 ◽  
Vol 13 (29) ◽  
pp. 7993-8000 ◽  
Author(s):  
Yu-Xin Gong ◽  
Qiong Wu ◽  
Hong-Hao Zhang ◽  
Qiu-Ning Zhu ◽  
Feng Shi
Keyword(s):  
Phosphoric Acid ◽  
Asymmetric Reactions ◽  
Asymmetric Reaction ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed ◽  
Catalytic Asymmetric ◽  
Catalytic Asymmetric Reactions

A chiral phosphoric acid-catalyzed asymmetric reaction of 2-indolylmethanols with 3-alkylindoles has been established to construct 2,2′-bisindolylmethane scaffold in good enantioselectivities.

Chiral Phosphoric Acid Catalyzed Regio- and Enantioselective Reactions of Functionalized Propargylic Alcohols

2022 ◽  
Author(s):  
Chenxiao Qian ◽  
Meiwen Liu ◽  
Jianwei Sun ◽  
Pengfei Li
Keyword(s):  
Phosphoric Acid ◽  
Asymmetric Reactions ◽  
Propargylic Alcohols ◽  
Chiral Phosphoric Acid ◽  
Wide Range ◽  
Enantioselective Reactions ◽  
Acid Catalyzed ◽  
Catalyzed Reactions ◽  
Phosphoric Acids

Propargylic alcohols have been known as useful substrates in a wide range of asymmetric reactions. Particularly, the chiral phosphoric acids (CPAs) catalyzed reactions of functionalized propargylic alcohols opened a robust...

Recent Advances in Chiral Phosphoric Acid Catalyzed Asymmetric Reactions for the Synthesis of Enantiopure Indole Derivatives

Synthesis ◽  
2015 ◽  
Vol 47 (14) ◽  
pp. 1990-2016 ◽  
Author(s):  
Hua Wu ◽  
Feng Shi ◽  
Yu-Ping He
Keyword(s):  
Phosphoric Acid ◽  
Asymmetric Reactions ◽  
Indole Derivatives ◽  
Recent Advances ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed

Insights into the Chiral Phosphoric Acid-Catalyzed Dynamic Kinetic Asymmetric Hydroamination of Racemic Allenes: An Allyl Carbocation/Phosphate Pair Mechanism

2021 ◽  
Vol 86 (5) ◽  
pp. 4121-4130
Author(s):  
Yuting Qiu ◽  
Haiyan Yuan ◽  
Xiaoying Zhang ◽  
Jingping Zhang
Keyword(s):  
Phosphoric Acid ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed

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.

Chiral Phosphoric Acid Catalyzed Stereoselective Spiroketalizations

Synlett ◽  
2013 ◽  
Vol 24 (06) ◽  
pp. 661-665 ◽  
Author(s):  
Pavel Nagorny ◽  
Zhankui Sun ◽  
Grace Winschel
Keyword(s):  
Phosphoric Acid ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed
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