Brønsted Acid-Catalyzed Enantioselective and Para-Selective Addition of Phenols to 1-Alkynylnaphth-2-Ols

被引：0

作者：

Dahiya, Anjali ^{[1
]}

Dhara, Kalyan ^{[1
]}

Garo, Jordan ^{[2
]}

Gicquiaud, Julien ^{[1
]}

Karnat, Alexandre ^{[1
]}

Berlande, Murielle ^{[1
]}

Hermange, Philippe ^{[1
]}

Sotiropoulos, Jean-Marc ^{[2
]}

Toullec, Patrick Y. ^{[1
]}

机构：

[1] Univ Bordeaux, CNRS, ISM, Bordeaux INP,UMR 5255, F-33400 Talence, France

[2] Univ Pau & Pays Adour, Inst Sci Analyt & Physico Chim Environm & Mat IPRE, CNRS, UMR 5254, 2 Ave President Angot,Helioparc, F-64053 Pau 09, France

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2025年

关键词：

Chiral br & oslash; nsted acids; Axially chiral alkenes; Vinylidene-quinone-methide intermediates; Phenols; Enantioselective Friedel-Crafts reaction; FRIEDEL-CRAFTS REACTIONS; ELECTRON-RICH PHENOLS; BASIS-SET; CONSTRUCTION; ALKYLATION; NAPHTHOLS; ATROPISOMERS; KETIMINES; ENERGIES; III;

D O I：

10.1002/adsc.202401457

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A chiral Br & oslash;nsted acid-catalyzed synthesis of axially chiral alkenes was developed via an enantioselective and para-selective Friedel-Crafts reaction between phenols and 1-alkynylnaphth-2-ols. This methodology features an efficient hydroarylation with high functional group tolerance, complete para-selectivity, excellent yields (up to 99%), and enantioselectivities (up to 94% ee) in the presence of a N-triflylphosphoramide catalyst. DFT calculations were performed to investigate para-selectivity and results indicate that both kinetics and thermodynamics parameters are more favorable compared to ortho-selectivity.

引用

页数：7

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