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.

A chiral Brønsted acid-catalyzed highly enantioselective Mannich-type reaction of α-diazo esters with in situ generated N-acyl ketimines

2018 ◽  
Vol 54 (28) ◽  
pp. 3516-3519 ◽  
Author(s):  
Rajshekhar A. Unhale ◽  
Milon M. Sadhu ◽  
Sumit K. Ray ◽  
Rayhan G. Biswas ◽  
Vinod K. Singh
Keyword(s):  
Phosphoric Acid ◽  
Reaction Conditions ◽  
Type Reaction ◽  
Chiral Phosphoric Acid ◽  
Brönsted Acid ◽  
Diazo Esters ◽  
Reaction Proceeds ◽  
Acid Catalyzed ◽  
Chiral Bronsted Acid

A chiral phosphoric acid-catalyzed asymmetric Mannich-type reaction of α-diazo esters with in situ generated N-acyl ketimines, derived from 3-aryl-3-hydroxyisoindolinones has been demonstrated. The reaction proceeds smoothly under mild reaction conditions.

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

scholarly journals Synthesis of six-membered spirooxindolesviaa chiral Brønsted acid-catalyzed asymmetric intramolecular Friedel–Crafts reaction

RSC Advances ◽  
2018 ◽  
Vol 8 (65) ◽  
pp. 37035-37039 ◽  
Author(s):  
Hui-Xuan Chen ◽  
Yaqi Zhang ◽  
Yuyang Zhang ◽  
Xuefeng He ◽  
Zhen-Wei Zhang ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Chiral Phosphoric Acid ◽  
Brönsted Acid ◽  
Acid Catalyzed ◽  
Chiral Bronsted Acid

A chiral phosphoric acid-catalyzed asymmetric intramolecular Friedel–Crafts reaction for the synthesis of 3′,4′-dihydro-2′H-spiro[indoline-3,1′-pyrrolo[1,2-a]pyrazin]-2-ones.

Asymmetric synthesis of CF3- and indole-containing tetrahydro-β-carbolines via chiral spirocyclic phosphoric acid-catalyzed aza-Friedel–Crafts reaction

2017 ◽  
Vol 4 (7) ◽  
pp. 1407-1410 ◽  
Author(s):  
En Xie ◽  
Abdul Rahman ◽  
Xufeng Lin
Keyword(s):  
Phosphoric Acid ◽  
Asymmetric Synthesis ◽  
Acid Catalysis ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed ◽  
Quaternary Stereocenter

An enantioselective aza-Friedel–Crafts reaction of indoles with 1-trifluoromethyl-3,4-dihydro-β-carbolines has been developed to afford tetrahydro-β-carbolines with a CF3- and indole-containing quaternary stereocenter by using chiral phosphoric acid catalysis.

Chiral Phosphoric Acid-Catalyzed Enantioselective [4+3] Cyclization Reaction of 4-Indolylmethanols and Quinone Esters

Synlett ◽  
2021 ◽  
Author(s):  
Zhouli Chen ◽  
Lei Wang ◽  
Yiheng Qian ◽  
Xufeng Lin
Keyword(s):  
Phosphoric Acid ◽  
Cyclization Reaction ◽  
Reaction Conditions ◽  
Efficient Access ◽  
Single Diastereomer ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed ◽  
Phosphoric Acids

An asymmetric [4+3] cyclization reaction of racemic 4-indolylmethanols and quinone esters catalyzed by chiral phosphoric acids has been developed. This method provides efficient access to biologically important benzoxepino[5,4,3-cd] indoles featuring both axial and central chirality in good yields with up to 98% ee and essentially single diastereomer in mild reaction conditions.

scholarly journals Chiral phosphoric acid-catalyzed stereodivergent synthesis of trisubstituted allenes and computational mechanistic studies

2020 ◽  
Vol 11 (1) ◽  
Author(s):  
Jiawen Wang ◽  
Sujuan Zheng ◽  
Subramani Rajkumar ◽  
Jinglei Xie ◽  
Na Yu ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Density Functional ◽  
Acid Catalysis ◽  
Chiral Molecules ◽  
Functional Theory ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed ◽  
Asymmetric Additions ◽  
Formation Step ◽  
Stagger Form

Abstract Chiral molecules with multiple stereocenters are widely present in natural products and pharmaceuticals, whose absolute and relative configurations are both critically important for their physiological activities. In spite of the fact that a series of ingenious strategies have been developed for asymmetric diastereodivergent catalysis, most of these methods are limited to the divergent construction of point chirality. Here we report an enantioselective and diastereodivergent synthesis of trisubstituted allenes by asymmetric additions of oxazolones to activated 1,3-enynes enabled by chiral phosphoric acid (CPA) catalysis, where the divergence of the allenic axial stereogenicity is realized by modifications of CPA catalysts. Density functional theory (DFT) calculations are performed to elucidate the origin of diastereodivergence by the stacking- and stagger-form in the transition state (TS) of allene formation step, as well as to disclose a Münchnone-type activation mode of oxazolones under Brønsted acid catalysis.

The control effects of different scaffolds in chiral phosphoric acids: a case study of enantioselective asymmetric arylation

2019 ◽  
Vol 9 (22) ◽  
pp. 6482-6491 ◽  
Author(s):  
Lihan Zhu ◽  
Hend Mohamed ◽  
Haiyan Yuan ◽  
Jingping Zhang
Keyword(s):  
Phosphoric Acid ◽  
Dft Calculations ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed ◽  
Catalyzed Reactions ◽  
Phosphoric Acids

DFT calculations disclosed that the sign of enantioselectivity in chiral-phosphoric-acid catalyzed reactions can be tuned by BINOL- or SPINOL-derived backbones.

scholarly journals Chiral Brønsted acid-catalyzed enantioselective Friedel–Crafts reaction of 2-methoxyfuran with aliphatic ketimines generated in situ

2016 ◽  
Vol 7 (2) ◽  
pp. 1057-1062 ◽  
Author(s):  
Azusa Kondoh ◽  
Yusuke Ota ◽  
Takazumi Komuro ◽  
Fuyuki Egawa ◽  
Kyohei Kanomata ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Acid Catalyst ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Chiral Phosphoric Acid ◽  
Brönsted Acid ◽  
Acid Catalyzed ◽  
Chiral Bronsted Acid

An enantioselective Friedel–Crafts reaction with aliphatic ketimines generated in situ from hemiaminal ethers afforded products with high enantioselectivity under the influence of a chiral phosphoric acid catalyst.

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.

Chiral phosphoric acid catalysis: from numbers to insights

2018 ◽  
Vol 47 (4) ◽  
pp. 1142-1158 ◽  
Author(s):  
Rajat Maji ◽  
Sharath Chandra Mallojjala ◽  
Steven E. Wheeler
Keyword(s):  
Phosphoric Acid ◽  
Quantum Chemistry ◽  
Acid Catalysis ◽  
Asymmetric Reactions ◽  
Computational Quantum Chemistry ◽  
Chiral Phosphoric Acid ◽  
Computational Quantum ◽  
Phosphoric Acids

Chiral phosphoric acids (CPAs) have emerged as powerful organocatalysts for asymmetric reactions, and applications of computational quantum chemistry have revealed important insights into the activity and selectivity of these catalysts.

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