The first catalytic asymmetric thioacetalization by chiral phosphoric acid catalysis

2016 ◽  
Vol 14 (7) ◽  
pp. 2205-2209 ◽  
Author(s):  
Jin-Sheng Yu ◽  
Wen-Biao Wu ◽  
Feng Zhou
Keyword(s):  
Phosphoric Acid ◽  
Acid Catalysis ◽  
Mild Conditions ◽  
Chiral Phosphoric Acid ◽  
Catalytic Asymmetric

We report here the first catalytic asymmetric thioacetalization of salicylaldehyde and dithiol. Chiral phosphoric acid STRIP C5 is identified as a powerful catalyst for this reaction to afford various chiral dithioacetals in high to excellent yields and enantioselectivities under mild conditions.

scholarly journals Organocatalytic enantioselective dearomatization of thiophenes by 1,10-conjugate addition of indole imine methides

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Xingguang Li ◽  
Meng Duan ◽  
Peiyuan Yu ◽  
K. N. Houk ◽  
Jianwei Sun
Keyword(s):  
Hydrogen Bonding ◽  
Phosphoric Acid ◽  
Nucleophilic Addition ◽  
Acid Catalysis ◽  
Conjugate Addition ◽  
Mild Conditions ◽  
Rapid Construction ◽  
Chiral Phosphoric Acid ◽  
Cyclic Molecules ◽  
Selectivity Control

AbstractCatalytic asymmetric dearomatization (CADA) is a powerful tool for the rapid construction of diverse chiral cyclic molecules from cheap and easily available arenes. This work reports an organocatalytic enantioselective dearomatization of substituted thiophenes in the context of a rare remote asymmetric 1,10-conjugate addition. By suitable stabilization of the thiophenyl carbocation with an indole motif in the form of indole imine methide, excellent remote chemo-, regio-, and stereocontrol in the nucleophilic addition can be achieved with chiral phosphoric acid catalysis under mild conditions. This protocol can be successfully extended to the asymmetric dearomatization of other heteroarenes including selenophenes and furans. Control experiments and DFT calculations demonstrate a possible pathway in which hydrogen bonding plays an important role in selectivity control.

scholarly journals Organocatalytic Asymmetric [2 + 4] Cycloadditions of 3-Vinylindoles with ortho-Quinone Methides

Molecules ◽  
2021 ◽  
Vol 26 (21) ◽  
pp. 6751
Author(s):  
Si-Jia Liu ◽  
Man-Su Tu ◽  
Kai-Yue Liu ◽  
Jia-Yi Chen ◽  
Shao-Fei Ni ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Structural Diversity ◽  
Quinone Methides ◽  
Chiral Phosphoric Acid ◽  
Catalytic Asymmetric ◽  
High Yields ◽  
Asymmetric Cycloadditions

Catalytic asymmetric [2 + 4] cycloadditions of 3-vinylindoles with ortho-quinone methides and their precursors were carried out in the presence of chiral phosphoric acid to afford a series of indole-containing chroman derivatives with structural diversity in overall high yields (up to 98%), good diastereoselectivities (up to 93:7 dr) and moderate to excellent enantioselectivities (up to 98% ee). This approach not only enriches the chemistry of catalytic asymmetric cycloadditions involving 3-vinylindoles but is also useful for synthesizing chiral chroman derivatives.

Asymmetric C-H and N-H functionalization of Indoles involving Central Chirality via Chiral Phosphoric Acid Catalysis

2021 ◽  
Vol 18 ◽  
Author(s):  
Alemayehu Gashaw ◽  
Dereje Kebebew Debeli ◽  
Meseret Chemeda
Keyword(s):  
Phosphoric Acid ◽  
Organic Compounds ◽  
Organic Synthesis ◽  
Acid Catalysis ◽  
Bond Formation ◽  
Acid Catalysts ◽  
Asymmetric Syntheses ◽  
Chiral Phosphoric Acid ◽  
Great Progress ◽  
Interesting Area

: The C-H and N-H functionalization of indoles is an interesting area of research that has a useful impact on organic synthesis due to the availability of chiral indole scaffolds in the discovery of drugs, synthetic bioactive compounds, and natural products. The chiral phosphoric acid catalysts (CPAs) have proven to be a powerful and versatile class of enantioselective organocatalysts. Many asymmetric syntheses of organic compounds have been carried out with these catalysts in C–C and C-N bond formation reactions, and great progress has been reported. By 2011, several reviews were published covering some important topics and recent achievements in this field. Therefore, in this review, the most recent advances, research breakthroughs with key examples involving mechanisms of CPA-catalyzed C-H and N-H functionalization of indoles to form central chirality via Friedel Crafts, Michael type, and rearrangement reactions were reviewed and reported.

Catalytic Asymmetric Substitution Reaction of 3-Substituted 2-Indolylmethanols with 2-Naphthols

Synthesis ◽  
2020 ◽  
Vol 52 (23) ◽  
pp. 3684-3692
Author(s):  
Feng Gao ◽  
Yu-Chen Zhang ◽  
Feng Shi ◽  
Jin-Ping Lan ◽  
Yi-Nan Lu ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Substitution Reaction ◽  
Enantioselective Synthesis ◽  
Chiral Phosphoric Acid ◽  
Catalytic Asymmetric ◽  
High Yields

A catalytic asymmetric substitution of 3-substituted 2-indolylmethanols with 2-naphthols has been established under the catalysis of chiral phosphoric acid. By this approach, a series of structurally diversified triarylmethane derivatives were obtained in moderate to high yields with good enantioselectivities (up to 97% yield, 95:5 er). This approach not only enriches the chemistry of 2-indolylmethanol-inolved catalytic asymmetric substitutions, but also provides a useful method for the enantioselective synthesis of chiral triarylmethane derivatives.

Enantioselective transfer hydrogenation, a key step for the synthesis of 3-aminotetrahydroquinolines

2016 ◽  
Vol 40 (11) ◽  
pp. 9034-9037 ◽  
Author(s):  
Alexandre Aillerie ◽  
Vincent Lemau de Talencé ◽  
Clément Dumont ◽  
Sylvain Pellegrini ◽  
Frédéric Capet ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Catalytic Amount ◽  
Transfer Hydrogenation ◽  
Mild Conditions ◽  
Chiral Phosphoric Acid

An enantioselective transfer hydrogenation has been successfully achieved to furnish 3-aminotetrahydroquinolines. The reaction was conducted in the presence of Hantzsch dihydropyridine and a catalytic amount of chiral phosphoric acid under mild conditions.

Construction of chiral chroman scaffolds via catalytic asymmetric (4 + 2) cyclizations of para-quinone methide derivatives with 3-vinylindoles

2020 ◽  
Vol 18 (28) ◽  
pp. 5388-5399 ◽  
Author(s):  
Shu-Fang Wu ◽  
Man-Su Tu ◽  
Qing-Qing Hang ◽  
Shu Zhang ◽  
Haixia Ding ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Quinone Methide ◽  
Title Reaction ◽  
Chiral Phosphoric Acid ◽  
Catalytic Asymmetric ◽  
High Yields

The title reaction has been established in the presence of chiral phosphoric acid, affording chiral chroman derivatives bearing an indole moiety in high yields and with moderate to good stereoselectivities.

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.

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.

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