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.

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.

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.

Enantioselective Synthesis of 1-Substituted 1,2,3,4-Tetrahydroisoquinolines through 1,3-Dipolar Cycloaddition by a Chiral Phosphoric Acid

Synlett ◽  
2019 ◽  
Vol 30 (13) ◽  
pp. 1541-1545 ◽  
Author(s):  
Yuan Jin ◽  
Yasuhiro Honma ◽  
Hisashi Morita ◽  
Masamichi Miyagawa ◽  
Takahiko Akiyama
Keyword(s):  
Phosphoric Acid ◽  
Asymmetric Synthesis ◽  
Vinyl Ether ◽  
31P Nmr ◽  
Cycloaddition Reaction ◽  
Enantioselective Synthesis ◽  
Dipolar Cycloaddition ◽  
New Approach ◽  
Chiral Phosphoric Acid ◽  
High Yields

A new approach is described for the asymmetric synthesis of 1-substituted 1,2,3,4-tetrahydroisoquinolines that is based on the enantioselective 1,3-dipolar cycloaddition reaction of a nitrone and a vinyl ether in the presence of a chiral phosphoric acid that gives the chiral tetrahydroisoquinolines in high yields and with high enantioselectivities. 1H and 31P NMR analyses of the mixture of nitrone and chiral phosphoric acid suggest the formation of a 1:1 complex.

Enantioselective synthesis of cyclic quaternary α-amino acid derivatives by chiral phosphoric acid catalysis

2017 ◽  
Vol 15 (28) ◽  
pp. 6033-6041 ◽  
Author(s):  
Lei Wang ◽  
Abdul Rahman ◽  
Xufeng Lin
Keyword(s):  
Amino Acid ◽  
Phosphoric Acid ◽  
Acid Catalysis ◽  
Enantioselective Synthesis ◽  
Amino Acid Derivatives ◽  
Chiral Phosphoric Acid ◽  
Efficient Route ◽  
Quaternary Stereocenter ◽  
High Yields ◽  
Phosphoric Acids

Development of highly enantioselective aza-Friedel–Crafts reaction of N-sulfonyl cyclic ketimines with indoles catalyzed by chiral phosphoric acids, providing an efficient route to indole-containing chiral cyclic α-amino acid derivatives bearing quaternary stereocenter in high yields and up to 98% enantioselectivity.

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

An organocatalytic asymmetric Friedel–Crafts reaction of 2-substituted indoles with aldehydes: enantioselective synthesis of α-hydroxyl ketones by low loading of chiral phosphoric acid

2020 ◽  
Vol 56 (16) ◽  
pp. 2499-2502 ◽  
Author(s):  
Xiong-fei Deng ◽  
Ying-wei Wang ◽  
Shi-qi Zhang ◽  
Ling Li ◽  
Guang-xun Li ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Carbonyl Compound ◽  
Enantioselective Synthesis ◽  
Chiral Phosphoric Acid

Hydroxyl alkylation of indoles by Friedel–Crafts reaction with a carbonyl compound is a useful strategy.

Highly Diastereo- and Enantioselective Synthesis of Cyclohepta[b ]indoles by Chiral-Phosphoric-Acid-Catalyzed (4+3) Cycloaddition

2018 ◽  
Vol 130 (37) ◽  
pp. 12297-12301 ◽  
Author(s):  
Coralie Gelis ◽  
Guillaume Levitre ◽  
Jérémy Merad ◽  
Pascal Retailleau ◽  
Luc Neuville ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Enantioselective Synthesis ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed

scholarly journals Modular synthesis of the pyrimidine core of the manzacidins by divergent Tsuji–Trost coupling

2016 ◽  
Vol 12 ◽  
pp. 1111-1121 ◽  
Author(s):  
Sebastian Bretzke ◽  
Stephan Scheeff ◽  
Felicitas Vollmeyer ◽  
Friederike Eberhagen ◽  
Frank Rominger ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Substitution Reaction ◽  
Grignard Reagent ◽  
Design Development ◽  
Practical Application ◽  
Efficient Procedure ◽  
Modular Synthesis ◽  
Cross Metathesis ◽  
Facile Preparation ◽  
High Yields

The design, development and application of an efficient procedure for the concise synthesis of the 1,3-syn- and anti-tetrahydropyrimidine cores of manzacidins are reported. The intramolecular allylic substitution reaction of a readily available joint urea-type substrate enables the facile preparation of both diastereomers in high yields. The practical application of this approach is demonstrated in the efficient and modular preparation of the authentic heterocyclic cores of manzacidins, structurally unique bromopyrrole alkaloids of marine origin. Additional features of this route include the stereoselective generation of the central amine core with an appending quaternary center by an asymmetric addition of a Grignard reagent to a chiral tert-butanesulfinyl ketimine following an optimized Ellman protocol and a cross-metathesis of a challenging homoallylic urea substrate, which proceeds in good yields in the presence of an organic phosphoric acid.

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