Brønsted Acid-Catalyzed, Highly Enantioselective Addition of Enamides to In Situ-Generatedortho-Quinone Methides: A Domino Approach to Complex Acetamidotetrahydroxanthenes

Hydrogen-bonded, in situ-generated ortho-quinone methides undergo highly enantioselective Friedel–Crafts reactions with indoles and naphthols under mild reaction conditions.

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Brønsted Acid-Catalyzed Enantioselective Addition of 1,3-Diones to in situ Generated N-Acyl Ketimines

Organic & Biomolecular Chemistry ◽

10.1039/d1ob02162a ◽

2021 ◽

Author(s):

Milon Mohan Sadhu ◽

Sumit Kumar Ray ◽

Rajshekhar A. Unhale ◽

Vinod K. Singh

Keyword(s):

Bronsted Acid ◽

Brønsted Acid ◽

Quaternary Carbon ◽

Brönsted Acid ◽

Acid Catalyzed ◽

Enantioselective Addition

A Brønsted acid-catalyzed asymmetric Mannich-type addition of 1,3-diones to cyclic N-acyl ketimines is reported for the synthesis of enantioenriched isoindolinones. Various dicarbonyl-substituted isoindolinones bearing quaternary carbon stereocenter were synthesized with...

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Brønsted Acid-Catalyzed Formal (3+3)-Annulation of Propargylic (Aza)-para-Quinone Methides with 4-Hydroxycoumarins and 1,3-Dicarbonyl Compounds

The Journal of Organic Chemistry ◽

10.1021/acs.joc.0c02844 ◽

2021 ◽

Author(s):

Zong-Wang Qiu ◽

Xue-Tao Xu ◽

Han-Peng Pan ◽

Zhen-Sheng Jia ◽

Ai-Jun Ma ◽

...

Keyword(s):

Bronsted Acid ◽

Brønsted Acid ◽

Quinone Methides ◽

Dicarbonyl Compounds ◽

Brönsted Acid ◽

Acid Catalyzed

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Brønsted Acid Catalyzed [3+2]-Cycloaddition of 2-Vinylindoles with In Situ Generated 2-Methide-2H-indoles: Highly Enantioselective Synthesis of Pyrrolo[1,2-a]indoles

Chemistry - A European Journal ◽

10.1002/chem.201601020 ◽

2016 ◽

Vol 22 (21) ◽

pp. 7074-7078 ◽

Cited By ~ 57

Author(s):

Kalisankar Bera ◽

Christoph Schneider

Keyword(s):

Enantioselective Synthesis ◽

Bronsted Acid ◽

Brønsted Acid ◽

Brönsted Acid ◽

Acid Catalyzed

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Efficient Synthesis of Chromenes from Vinyl o-Quinone Methides via a Brønsted Acid Catalyzed Electrocyclization Process

Synthesis ◽

10.1055/s-0037-1609483 ◽

2018 ◽

Vol 50 (12) ◽

pp. 2416-2422 ◽

Cited By ~ 4

Author(s):

Man-Su Tu ◽

Guang-Jian Mei ◽

Feng Shi ◽

Si-Jia Liu ◽

Xiao-Li Jiang ◽

...

Keyword(s):

Efficient Method ◽

Research Area ◽

Environmentally Benign ◽

Bronsted Acid ◽

Brønsted Acid ◽

Efficient Synthesis ◽

Quinone Methides ◽

Efficient Approach ◽

Brönsted Acid ◽

Acid Catalyzed

An efficient approach for the synthesis of chromene derivatives from vinyl o-quinone methides was established via a Brønsted acid catalyzed electrocyclization. By using this methodology, a series of structurally diversified chromenes was synthesized in a highly atom-economic and environmentally benign manner with generally good to excellent yields (up to 98% yield). This reaction will not only provide an efficient method for the construction of chromene scaffolds, but also enrich the research area of o-quinone methides.

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Brønsted Acid-catalyzed Dynamic Kinetic Resolution of in situ Formed Acyclic N,O-hemiaminals: Cascade Synthesis of Chiral Cyclic N,O-aminals

Organic Chemistry Frontiers ◽

10.1039/d1qo01135a ◽

2021 ◽

Author(s):

Xue-Jiao Lv ◽

Yong-Chao Ming ◽

Hui-Chun Wu ◽

Yankai Liu

Keyword(s):

Kinetic Resolution ◽

Michael Reaction ◽

Amide Group ◽

Bronsted Acid ◽

Brønsted Acid ◽

Dynamic Kinetic Resolution ◽

Brönsted Acid ◽

Acid Catalyzed

A Brønsted acid-catalyzed cascade acyclic N,O-hemiaminal formation/oxa-Michael reaction is developed for the synthesis of cis-2,6-disubstituted tetrahydropyrans bearing an exo amide group, that is, cyclic N,O-aminals. By using TsOH, various different...

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