Enantioselective Construction of Tetrasubstituted Center of Chirality in Isoindolinones via Organocatalyzed Reaction Between Ketones and N-Acyl Ketimines

2021 ◽  
Author(s):  
Mateja Matišić ◽  
Matija Gredičak
Keyword(s):  
Phosphoric Acid ◽  
Chiral Phosphoric Acid ◽  
Enantioselective Reaction

An efficient enantioselective reaction between ketones and N-acyl ketimines is described. In a reaction catalyzed by a chiral phosphoric acid, a broad range of ketones and ketimines afforded isoindolinone derivatives...

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 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 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

Asymmetric Arylative Dearomatization of β-Naphthols Catalyzed by a Chiral Phosphoric Acid

2017 ◽  
Vol 23 (22) ◽  
pp. 5381-5385 ◽  
Author(s):  
Xiao-Qiang Li ◽  
Hui Yang ◽  
Jiao-Jiao Wang ◽  
Bo-Bo Gou ◽  
Jie Chen ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Chiral Phosphoric Acid

Direct Asymmetric α-Hydroxylation of Cyclic α-Branched Ketones through Enol Catalysis

Synlett ◽  
2018 ◽  
Vol 30 (01) ◽  
pp. 49-53 ◽  
Author(s):  
Benjamin List ◽  
Grigory Shevchenko ◽  
Gabriele Pupo
Keyword(s):  
Natural Products ◽  
Phosphoric Acid ◽  
Carbonyl Compounds ◽  
Tertiary Alcohols ◽  
Chiral Phosphoric Acid

Enantiopure α-hydroxy carbonyl compounds are common scaffolds in natural products and pharmaceuticals. Although indirect approaches towards their synthesis are known, direct asymmetric methodologies are scarce. Herein, we report the first direct asymmetric α-hydroxylation of α-branched ketones through enol catalysis, enabling a facile access to valuable α-keto tertiary alcohols. The transformation, characterized by the use of nitrosobenzene as the oxidant and a new chiral phosphoric acid as the catalyst, delivers a good scope and excellent enantioselectivities.

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