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.

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.

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.

Highly Enantioselective Biginelli Reaction of Aliphatic Aldehydes Catalyzed by Chiral Phosphoric Acids

Synlett ◽  
2017 ◽  
Vol 28 (15) ◽  
pp. 2041-2045 ◽  
Author(s):  
Yongbiao Guo ◽  
Chuanpin Zou ◽  
Zhenhua Gao ◽  
Xiangyan Meng ◽  
Guilan Huang ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Biginelli Reaction ◽  
Aliphatic Aldehyde ◽  
Reaction Conditions ◽  
Aliphatic Aldehydes ◽  
Keto Ester ◽  
Chiral Phosphoric Acid ◽  
Three Component Reaction ◽  
High Yields ◽  
Phosphoric Acids

Several chiral phosphoric acids were evaluated as organocatalysts for the enantioselective Biginelli reaction of aliphatic aldehydes. With a chiral phosphoric acid derived from 3,3′-bis(3,5-di-tert-butyl-4-methoxyphenyl)-1,1′-binaphthalene-2,2′-diol, and after extensive optimization of the reaction conditions, the corresponding dihydropyrimidines were obtained in moderate to high yields with 73–87% ee by a three-component reaction of an aliphatic aldehyde, urea, and a β-keto ester.

scholarly journals Organocatalytic asymmetric selenofunctionalization of tryptamine for the synthesis of hexahydropyrrolo[2,3-b]indole derivatives

2013 ◽  
Vol 9 ◽  
pp. 1559-1564 ◽  
Author(s):  
Qiang Wei ◽  
Ya-Yi Wang ◽  
Yu-Liu Du ◽  
Liu-Zhu Gong
Keyword(s):  
Phosphoric Acid ◽  
Indole Derivatives ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed ◽  
High Yields

A chiral phosphoric acid-catalyzed selenofunctionalization of tryptamine derivatives provides access to 3a-(phenylselenyl)-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole derivatives in high yields and with synthetically useful levels of enantioselectivity (up to 89% ee).

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.

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.

Enantioselective construction of a 2,2′-bisindolylmethane scaffold via catalytic asymmetric reactions of 2-indolylmethanols with 3-alkylindoles

2015 ◽  
Vol 13 (29) ◽  
pp. 7993-8000 ◽  
Author(s):  
Yu-Xin Gong ◽  
Qiong Wu ◽  
Hong-Hao Zhang ◽  
Qiu-Ning Zhu ◽  
Feng Shi
Keyword(s):  
Phosphoric Acid ◽  
Asymmetric Reactions ◽  
Asymmetric Reaction ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed ◽  
Catalytic Asymmetric ◽  
Catalytic Asymmetric Reactions

A chiral phosphoric acid-catalyzed asymmetric reaction of 2-indolylmethanols with 3-alkylindoles has been established to construct 2,2′-bisindolylmethane scaffold in good enantioselectivities.

Enantioselective Biginelli Reaction of Aliphatic Aldehydes Catalyzed by a Chiral Phosphoric Acid: A Key Step in the Synthesis of the Bicyclic Guanidine Core of Crambescin A and Batzelladine A

Synthesis ◽  
2018 ◽  
Vol 50 (12) ◽  
pp. 2394-2406 ◽  
Author(s):  
Yongbiao Guo ◽  
Chuanpin Zou ◽  
Zhenhua Gao ◽  
Chongxu Fan ◽  
Jisheng Chen ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Biginelli Reaction ◽  
Aliphatic Aldehydes ◽  
Formal Synthesis ◽  
Chiral Phosphoric Acid ◽  
Wide Range ◽  
Synthetic Utility ◽  
Acid Catalyzed ◽  
High Yields ◽  
Optically Pure

An efficient chiral phosphoric acid catalyzed Biginelli reaction for the synthesis of optically pure 4-alkyl-3,4-dihydropyrimidin-2-(1H)-ones has been developed, with a wide range of the desired products being obtained in moderate to high yields with good to excellent enantioselectivities (up to >99% ee after one recrystallization). The synthetic utility of this reaction is illustrated in various aliphatic bicyclic guanidine compounds, which is applied in the formal synthesis of the bicyclic guanidine core of crambescin A and batzelladine A.

Chiral phosphoric acid catalyzed oxidative kinetic resolution of cyclic secondary amine derivatives including tetrahydroquinolines by hydrogen transfer to imines

2015 ◽  
Vol 51 (93) ◽  
pp. 16648-16651 ◽  
Author(s):  
Kodai Saito ◽  
Hiromitsu Miyashita ◽  
Takahiko Akiyama
Keyword(s):  
Phosphoric Acid ◽  
Secondary Amine ◽  
Hydrogen Transfer ◽  
Kinetic Resolution ◽  
Title Reaction ◽  
Efficient Conversion ◽  
Chiral Phosphoric Acid ◽  
Oxidative Kinetic Resolution ◽  
Acid Catalyzed

The title reaction of tetrahydroquinolines with ketimine in the presence of chiral phosphoric acid proceeded with efficient conversion and excellent enantioselectivities.

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