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.

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

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.

Asymmetric synthesis of atropisomeric pyrazole via an enantioselective reaction of azonaphthalene with pyrazolone

2019 ◽  
Vol 55 (84) ◽  
pp. 12715-12718 ◽  
Author(s):  
Huijun Yuan ◽  
Yao Li ◽  
Hanhui Zhao ◽  
Zhihong Yang ◽  
Xin Li ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Asymmetric Synthesis ◽  
Pyrazole Derivatives ◽  
Asymmetric Reaction ◽  
Chiral Phosphoric Acid ◽  
Wide Range ◽  
Axially Chiral ◽  
Enantioselective Reaction ◽  
Catalytic Asymmetric

The first catalytic asymmetric reaction of azonaphthalene with pyrazolone has been established. A wide range of axially chiral pyrazole derivatives have been achieved in good yields (68–99%) with excellent enantioselectivities (83–98% ee) by utilizing chiral phosphoric acid as a catalyst.

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...

scholarly journals Enamides and dienamides in phosphoric acid-catalysed enantioselective cycloadditions for the synthesis of chiral amines

2021 ◽  
Vol 57 (34) ◽  
pp. 4089-4105
Author(s):  
Thomas Varlet ◽  
Géraldine Masson
Keyword(s):  
Phosphoric Acid ◽  
Chiral Amines ◽  
Feature Article ◽  
Cyclic Amines ◽  
Chiral Phosphoric Acid ◽  
Wide Range ◽  
Acid Catalyzed

This feature article describes how enamides and dienamides can participate in chiral phosphoric acid catalyzed enantioselective cycloadditions to prepare a wide range of cyclic amines.

Construction of Axially Chiral Styrene-Type Allylamines via Chiral Phosphoric Acid-Catalyzed Asymmetric Reductive Amination

2022 ◽  
Author(s):  
You-Dong Shao ◽  
Jin-Shuo Feng ◽  
Dan-Dan Han ◽  
Kang-Hui Pan ◽  
Ling Zhang ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Reductive Amination ◽  
Enantioselective Synthesis ◽  
Chiral Phosphoric Acid ◽  
Axially Chiral ◽  
Acid Catalyzed

The first enantioselective synthesis of axially chiral styrene-type allylamines was achieved through chiral phosphoric acid mediated atroposelective reductive amination of 1-enal substituted 2-naphthols. This protocol features a broad substrate scope,...

Enantioselective Biginelli Reaction of Aliphatic Aldehydes Catalyzed by a Chiral Phosphoric Acid: A Key Step in the Synthesis of the Bicyclic Guanidine Core of Crambescin A and Batzelladine A

Synthesis ◽  
2018 ◽  
Vol 50 (12) ◽  
pp. 2394-2406 ◽  
Author(s):  
Yongbiao Guo ◽  
Chuanpin Zou ◽  
Zhenhua Gao ◽  
Chongxu Fan ◽  
Jisheng Chen ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Biginelli Reaction ◽  
Aliphatic Aldehydes ◽  
Formal Synthesis ◽  
Chiral Phosphoric Acid ◽  
Wide Range ◽  
Synthetic Utility ◽  
Acid Catalyzed ◽  
High Yields ◽  
Optically Pure

An efficient chiral phosphoric acid catalyzed Biginelli reaction for the synthesis of optically pure 4-alkyl-3,4-dihydropyrimidin-2-(1H)-ones has been developed, with a wide range of the desired products being obtained in moderate to high yields with good to excellent enantioselectivities (up to >99% ee after one recrystallization). The synthetic utility of this reaction is illustrated in various aliphatic bicyclic guanidine compounds, which is applied in the formal synthesis of the bicyclic guanidine core of crambescin A and batzelladine A.

Organocatalytic regio-, diastereo- and enantioselective γ-additions of isoxazol-5(4H)-ones to β,γ-alkynyl-α-imino esters for the synthesis of axially chiral tetrasubstituted α-amino allenoates

2021 ◽  
Author(s):  
Fushuai Li ◽  
Shuai Liang ◽  
Yepeng Luan ◽  
Xuling Chen ◽  
Hanhui Zhao ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Chiral Phosphoric Acid ◽  
Axially Chiral ◽  
Enantioselective Reaction ◽  
Acid Catalyzed ◽  
Imino Esters

The chiral phosphoric acid catalyzed regio-, diastereo- and enantioselective reaction of isoxazol-5(4H)-ones with β,γ-alkynyl-α-imino esters has been developed.

scholarly journals Organocatalytic atroposelective synthesis of axially chiral styrenes

2017 ◽  
Vol 8 (1) ◽  
Author(s):  
Sheng-Cai Zheng ◽  
San Wu ◽  
Qinghai Zhou ◽  
Lung Wa Chung ◽  
Liu Ye ◽  
...  
Keyword(s):  
Asymmetric Catalysis ◽  
Addition Reaction ◽  
Building Blocks ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Active Compounds ◽  
Chiral Compounds ◽  
Axially Chiral ◽  
Potential Applications ◽  
Styrene Derivatives

Abstract Axially chiral compounds are widespread in biologically active compounds and are useful chiral ligands or organocatalysts in asymmetric catalysis. It is well-known that styrenes are one of the most abundant and principal feedstocks and thus represent excellent prospective building blocks for chemical synthesis. Driven by the development of atroposelective synthesis of axially chiral styrene derivatives, we discovered herein the asymmetric organocatalytic approach via direct Michael addition reaction of substituted diones/ketone esters/malononitrile to alkynals. The axially chiral styrene compounds were produced with good chemical yields, enantioselectivities and almost complete E/Z-selectivities through a secondary amine-catalysed iminium activation strategy under mild conditions. Such structural motifs are important precursors for further transformations into biologically active compounds and synthetic useful intermediates and may have potential applications in asymmetric synthesis as olefin ligands or organocatalysts.

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