scholarly journals Experimental and Computational Studies on Regiodivergent Chiral Phosphoric Acid Catalyzed Cycloisomerization of Mupirocin Methyl Ester

2020 ◽  
Vol 26 (20) ◽  
pp. 4583-4591 ◽  
Author(s):  
Sibin Wang ◽  
Alonso J. Arguelles ◽  
Jia‐Hui Tay ◽  
Miyuki Hotta ◽  
Paul M. Zimmerman ◽  
...  
Keyword(s):  
Methyl Ester ◽  
Phosphoric Acid ◽  
Computational Studies ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed

Secondary stereocontrolling interactions in chiral Brønsted acid catalysis: study of a Petasis–Ferrier-type rearrangement catalyzed by chiral phosphoric acids

2014 ◽  
Vol 5 (9) ◽  
pp. 3515-3523 ◽  
Author(s):  
Kyohei Kanomata ◽  
Yasunori Toda ◽  
Yukihiro Shibata ◽  
Masahiro Yamanaka ◽  
Seiji Tsuzuki ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Phosphoric Acid ◽  
Acid Catalysis ◽  
Computational Studies ◽  
Stacking Interactions ◽  
Π Stacking ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed ◽  
Chiral Bronsted Acid ◽  
Phosphoric Acids

Guided by computational studies, the involvement of non-classical C–H⋯O hydrogen bonds and π–π stacking interactions were found to be crucial for high stereocontrol in a chiral phosphoric acid-catalyzed reaction.

Asymmetric phosphoric acid–catalyzed four-component Ugi reaction

Science ◽  
2018 ◽  
Vol 361 (6407) ◽  
pp. eaas8707 ◽  
Author(s):  
Jian Zhang ◽  
Peiyuan Yu ◽  
Shao-Yu Li ◽  
He Sun ◽  
Shao-Hua Xiang ◽  
...  
Keyword(s):  
Reaction Mechanism ◽  
Carboxylic Acid ◽  
Phosphoric Acid ◽  
Enantiomeric Excess ◽  
Structural Diversity ◽  
Ugi Reaction ◽  
Computational Studies ◽  
Formidable Challenge ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed

The Ugi reaction constructs α-acylaminoamide compounds by combining an aldehyde or ketone, an amine, a carboxylic acid, and an isocyanide in a single flask. Its appealing features include inherent atom and step economy together with the potential to generate products of broad structural diversity. However, control of the stereochemistry in this reaction has proven to be a formidable challenge. We describe an efficient enantioselective four-component Ugi reaction catalyzed by a chiral phosphoric acid derivative that delivers more than 80 α-acylaminoamides in good to excellent enantiomeric excess. Experimental and computational studies establish the reaction mechanism and origins of stereoselectivity.

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

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 Identifying the true origins of selectivity in chiral phosphoric acid catalyzed N-acyl-azetidine desymmetrizations

2021 ◽  
Author(s):  
Pier Alexandre Champagne
Keyword(s):  
Phosphoric Acid ◽  
Chiral Phosphoric Acid ◽  
Transition Structures ◽  
Acid Catalyzed

The origins of selectivity in azetidine desymmetrizations have been determined computationally. Comparison of structures with model and full catalysts provided key details missed by typical analyses of the stereodetermining transition structures.

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.

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