Synthesis of 1,2,3,4-Tetrahydroquinolines including Angustureine and Congeneric Alkaloids. A Review

Díaz, Gaspar; Dudley, Gregory B.

doi:10.1080/00304948.2015.1025012

Cited by 41 publications

(10 citation statements)

References 63 publications

(36 reference statements)

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“…Chiral tetrahydroquinolines (THQs) are widespread in pharmaceuticals and natural products (Figure a) . Their efficient construction has long been a goal for both organic and medicinal chemists . In addition to well-established cyclization reactions such as the Pavarov reaction, dearomatization of quinolines represents a straightforward and attractive method toward these scaffolds.…”

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confidence: 99%

Enantioselective Synthesis of 4-Aminotetrahydroquinolines via 1,2-Reductive Dearomatization of Quinolines and Copper(I) Hydride-Catalyzed Asymmetric Hydroamination

2019

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A 1,2-reductive dearomatization of quinolines and copper(II) acetate monohydrate/(R,R)-Ph-BPE/P(p-tolyl)3-catalyzed enantioselective hydroamination sequence was developed, affording diverse 4-amino-1,2,3,4-tetrahydroquinolines with high levels of enantioselectivity in either a stepwise or one-pot fashion. Pleasingly, internal cis-cyclic alkenes, which are challenging substrates in copper hydride-catalyzed enantioselective hydroamination reactions, were transformed efficiently under mild conditions.

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confidence: 99%

Enantioselective Synthesis of 4-Aminotetrahydroquinolines via 1,2-Reductive Dearomatization of Quinolines and Copper(I) Hydride-Catalyzed Asymmetric Hydroamination

2019

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“…[1][2][3][4] In past decades, many methods have been developed for their synthesis to meet various requirements in different fields. [5][6][7][8][9] Despite tremendous progress, the current methods are still subject to various limitations.…”

Section: Introductionmentioning

confidence: 99%

Catalytic Enantioselective Construction of Chiral Benzo-Fused N -Heterocycles through Friedel–Crafts-Type Electrophilic Chlorination

et al. 2022

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“…1 These compounds display, inter alia, antitumor, antiarrhythmic, antibiotic, antidepressant, cardiovascular, antithrombotic, antiallergenic, antiheumatic, immunosuppressant, and antifertility activity. 1 …”

Section: Introductionmentioning

confidence: 99%

Catalytic, Enantioselective, Intramolecular Sulfenoamination of Alkenes with Anilines

Denmark

Min

2017

J. Org. Chem.

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A method for the catalytic, enantioselective, intramolecular sulfenoamination of alkenes with aniline nucleophiles has been developed. The method employs a chiral, Lewis basic selenophosphoramide catalyst and a Brønsted acid co-catalyst to promote stereocontrolled C–N and C–S bond formation by activation of an achiral sulfenylating agent. Benzoannulated nitrogen-containing heterocycles such as indolines, tetrahydroquinolines, and tetrahydrobenzazepines were prepared with high to excellent enantioselectivities. The impact of tether length and electron density of both the nucleophile and olefin on the reactivity, site selectivity, and enantioselectivity were investigated and interpreted in terms of substrate-dependent stereodetermining thiiranium ion formation or capture.

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Synthesis of 1,2,3,4-Tetrahydroquinolines including Angustureine and Congeneric Alkaloids. A Review

Cited by 41 publications

References 63 publications

Enantioselective Synthesis of 4-Aminotetrahydroquinolines via 1,2-Reductive Dearomatization of Quinolines and Copper(I) Hydride-Catalyzed Asymmetric Hydroamination

Enantioselective Synthesis of 4-Aminotetrahydroquinolines via 1,2-Reductive Dearomatization of Quinolines and Copper(I) Hydride-Catalyzed Asymmetric Hydroamination

Catalytic Enantioselective Construction of Chiral Benzo-Fused N -Heterocycles through Friedel–Crafts-Type Electrophilic Chlorination

Catalytic, Enantioselective, Intramolecular Sulfenoamination of Alkenes with Anilines

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