Promising Combination for Asymmetric Organocatalysis: Brønsted Acid-Assisted Chiral Phosphoric Acid Catalysis

ChemCatChem ◽  
2014 ◽  
Vol 6 (12) ◽  
pp. 3309-3311 ◽  
Author(s):  
Rong Zhao ◽  
Lei Shi
Keyword(s):  
Phosphoric Acid ◽  
Acid Catalysis ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Chiral Phosphoric Acid ◽  
Brönsted Acid ◽  
Asymmetric Organocatalysis

Practical catalytic enantioselective synthesis of 2,3-dihydroquin-azolinones by chiral brønsted acid catalysis

2021 ◽  
Author(s):  
Yongbiao Guo ◽  
Zhenhua Gao ◽  
Junchen Li ◽  
Xiaojing Bi ◽  
Enxue Shi ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Acid Catalysis ◽  
Enantioselective Synthesis ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Brönsted Acid ◽  
Chiral Bronsted Acid ◽  
Bronsted Acid Catalysis

An efficient, practical and scalable protocol to prepare chiral 2,3-dihydroquinazolinones was developed under catalysis of spirocyclic SPINOL-phosphoric acid.

Chiral Brønsted Acid from Chiral Phosphoric Acid Boron Complex and Water: Asymmetric Reduction of Indoles

2020 ◽  
Vol 132 (8) ◽  
pp. 3320-3325 ◽  
Author(s):  
Kai Yang ◽  
Yixian Lou ◽  
Chenglan Wang ◽  
Liang‐Wen Qi ◽  
Tongchang Fang ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Asymmetric Reduction ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Chiral Phosphoric Acid ◽  
Brönsted Acid ◽  
Boron Complex ◽  
Chiral Bronsted Acid

scholarly journals An asymmetric Brønsted acid-catalyzed Friedel–Crafts reaction of indoles with cyclic N-sulfimines

RSC Advances ◽  
2017 ◽  
Vol 7 (54) ◽  
pp. 34283-34286 ◽  
Author(s):  
Sang Gyu Lee ◽  
Sung-Gon Kim
Keyword(s):  
Phosphoric Acid ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Chiral Phosphoric Acid ◽  
Brönsted Acid ◽  
Acid Catalyzed

A highly enantioselective organocatalytic Friedel–Crafts reaction of indoles with cyclic N-sulfimines using a chiral phosphoric acid as an organocatalyst has been developed.

Chiral Brønsted Acid from Chiral Phosphoric Acid Boron Complex and Water: Asymmetric Reduction of Indoles

2020 ◽  
Vol 59 (8) ◽  
pp. 3294-3299 ◽  
Author(s):  
Kai Yang ◽  
Yixian Lou ◽  
Chenglan Wang ◽  
Liang‐Wen Qi ◽  
Tongchang Fang ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Asymmetric Reduction ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Chiral Phosphoric Acid ◽  
Brönsted Acid ◽  
Boron Complex ◽  
Chiral Bronsted Acid

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.

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.

scholarly journals Brønsted acid catalysis – the effect of 3,3′-substituents on the structural space and the stabilization of imine/phosphoric acid complexes

2019 ◽  
Vol 10 (20) ◽  
pp. 5226-5234 ◽  
Author(s):  
Maxime Melikian ◽  
Johannes Gramüller ◽  
Johnny Hioe ◽  
Julian Greindl ◽  
Ruth M. Gschwind
Keyword(s):  
Phosphoric Acid ◽  
Acid Catalysis ◽  
Theoretical Studies ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Structural Space ◽  
Brönsted Acid ◽  
Bronsted Acid Catalysis

Advanced NMR and theoretical studies reveal detailed insights into monomeric and dimeric structures plus deviating experimental and theoretical E/Z-populations.

scholarly journals Brønsted Acid Catalysis—Structural Preferences and Mobility in Imine/Phosphoric Acid Complexes

2016 ◽  
Vol 138 (49) ◽  
pp. 15965-15971 ◽  
Author(s):  
Julian Greindl ◽  
Johnny Hioe ◽  
Nils Sorgenfrei ◽  
Fabio Morana ◽  
Ruth M. Gschwind
Keyword(s):  
Phosphoric Acid ◽  
Acid Catalysis ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Brönsted Acid ◽  
Structural Preferences ◽  
Bronsted Acid Catalysis

Chiral phosphoric acid-catalyzed direct asymmetric mannich reaction of cyclicC-acylimines with simple ketones: facile access to C2-quaternary indolin-3-ones

2018 ◽  
Vol 54 (66) ◽  
pp. 9151-9154 ◽  
Author(s):  
Jin-Shan Li ◽  
Yong-Jie Liu ◽  
Shen Li ◽  
Jun-An Ma
Keyword(s):  
Phosphoric Acid ◽  
Mannich Reaction ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Chiral Phosphoric Acid ◽  
Brönsted Acid ◽  
Acid Catalyzed ◽  
Chiral Bronsted Acid

A chiral Brønsted acid-catalyzed direct asymmetric Mannich reaction of simple ketones with cyclicC-acylimines has been established for the synthesis of C2-quaternary indolin-3-ones.

Access to chiral 1-aminoindene derivatives by asymmetric Brønsted acid catalysis

Synlett ◽  
2021 ◽  
Author(s):  
Xiang Wu
Keyword(s):  
Acid Catalysis ◽  
Symptomatic Treatment ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Brönsted Acid ◽  
Iminium Ion ◽  
Asymmetric Organocatalysis ◽  
Chiral Bronsted Acid ◽  
Synthetic Intermediate ◽  
Bronsted Acid Catalysis

Asymmetric organocatalysis is emerging as an elegant tool for accelerating chemical reactions and creating specific types of molecules. Chiral Brønsted acid catalysis is an important area of organocatalysis. Recently we described a chiral Brønsted acid (N-triflyl phosphoramide) catalyzed intramolecular iminium ion cyclization reaction of 2-alkenylbenzaldimines for the synthesis of chiral 1-aminoindenes and tetracyclic 1-aminoindanes in good yields and high enantioselectivities. The obtained 1-aminoindene can be utilized as useful synthetic intermediate for synthesis of (S)-rasagiline, an effective drug for the symptomatic treatment of Parkinson's disease. And the obtained tetracyclic 1-aminoindanes are the skeleton of homoisoflavanoid natural products such as brazilin.

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