Enantioselective Synthesis of anti-1,2-Oxaborinan-3-enes from Aldehydes and 1,1-Di(boryl)alk-3-enes Using Ruthenium and Chiral Phosphoric Acid Catalysts

2017 ◽  
Vol 139 (31) ◽  
pp. 10903-10908 ◽  
Author(s):  
Tomoya Miura ◽  
Junki Nakahashi ◽  
Wang Zhou ◽  
Yota Shiratori ◽  
Scott G. Stewart ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Enantioselective Synthesis ◽  
Acid Catalysts ◽  
Chiral Phosphoric Acid

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

scholarly journals QM/MM study on the enantioselectivity of spiroacetalization catalysed by an imidodiphosphoric acid catalyst: how confinement works

2016 ◽  
Vol 14 (11) ◽  
pp. 3031-3039 ◽  
Author(s):  
Luis Simón ◽  
Robert S. Paton
Keyword(s):  
Phosphoric Acid ◽  
Acid Catalyst ◽  
Acid Catalysts ◽  
Chiral Phosphoric Acid

An explanation of why confined imidodiphosphoric acid catalyst succeeds where other chiral phosphoric acid catalysts fail.

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.

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

Organocatalytic asymmetric synthesis of benzazepinoindole derivatives with trifluoromethylated quaternary stereocenters by chiral phosphoric acid catalysts

2018 ◽  
Vol 16 (8) ◽  
pp. 1367-1374 ◽  
Author(s):  
Abdul Rahman ◽  
En Xie ◽  
Xufeng Lin
Keyword(s):  
Phosphoric Acid ◽  
Asymmetric Synthesis ◽  
Acid Catalysts ◽  
Chiral Phosphoric Acid ◽  
Quaternary Stereocenters

An enantioselective aza-Friedel–Crafts reaction of trifluoromethyl dihydrobenzoazepinoindoles with pyrroles or indoles catalyzed by a chiral spirocyclic phosphoric acid was developed.

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