Brønsted Acid Catalyzed Domino 1,6-Addition/Intramolecular Cyclization­ Reactions: Diastereoselective Synthesis of Dihydro­coumarin Frameworks

Synthesis ◽  
2017 ◽  
Vol 50 (06) ◽  
pp. 1307-1314 ◽  
Author(s):  
Guang-Jian Mei ◽  
Zheng Cao ◽  
Gui-Xiang Zhou ◽  
Chun Ma ◽  
Kang Jiang
Keyword(s):  
Hydrogen Bonding ◽  
Crucial Role ◽  
Acid Catalysis ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Diastereoselective Synthesis ◽  
Quinone Methides ◽  
Hydrogen Bonding Interactions ◽  
Brönsted Acid ◽  
Acid Catalyzed

An efficient domino 1,6-addition/intramolecular cyclization reaction between para-quinone methides (p-QMs) and azlactones under Brønsted acid catalysis was established. A series of highly functionalized dihydrocoumarins were constructed in good to excellent yields (up to 96%) with excellent diastereoselectivities (all >20:1 d.r.). In this process, the Brønsted acid plays a crucial role not only in activating the two substrates, but also in controlling the diastereoselectivity of the reaction via hydrogen-bonding interactions. In addition, this protocol demonstrates the great practicability of utilizing p-QMs in domino reactions.

Brønsted acid catalyzed radical addition to quinone methides

2021 ◽  
Author(s):  
Shiv Shankar Patel ◽  
Dileep Kumar ◽  
Chandra Bhushan Tripathi
Keyword(s):  
Alkyl Radical ◽  
Acid Catalysis ◽  
Radical Addition ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Quinone Methides ◽  
Mild Conditions ◽  
Brönsted Acid ◽  
Acid Catalyzed ◽  
Radical Generation

A fundamental quest for alkyl radical generation under mild conditions through photoinduced Brønsted acid catalysis is addressed.

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

Synthesis ◽  
2018 ◽  
Vol 50 (12) ◽  
pp. 2416-2422 ◽  
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.

Brønsted acid-catalyzed 1,2-fluorine migration with fluoroepoxides

2015 ◽  
Vol 44 (45) ◽  
pp. 19636-19641 ◽  
Author(s):  
Tao Luo ◽  
Rui Zhang ◽  
Xiao Shen ◽  
Wei Zhang ◽  
Chuanfa Ni ◽  
...  
Keyword(s):  
Fluorine Atom ◽  
Acid Catalysis ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Atom Economy ◽  
Mild Conditions ◽  
Brönsted Acid ◽  
Acid Catalyzed ◽  
Bronsted Acid Catalysis

An efficient 1,2-fluorine migration reaction was realized under Brønsted acid catalysis in the absence of an external fluorinating source. The high fluorine atom economy and very mild conditions make this reaction a promising protocol for the construction of the C–F bond.

scholarly journals Correction: Diastereoselective synthesis of 1,3-disubstituted isoindolines and sultams via bronsted acid catalysis

2020 ◽  
Vol 56 (14) ◽  
pp. 2211-2213
Author(s):  
Ye Tao ◽  
Scott R. Gilbertson
Keyword(s):  
Acid Catalysis ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Diastereoselective Synthesis ◽  
Brönsted Acid ◽  
Bronsted Acid Catalysis

Correction for ‘Diastereoselective synthesis of 1,3-disubstituted isoindolines and sultams via bronsted acid catalysis’ by Ye Tao et al., Chem. Commun., 2018, 54, 11292–11295.

scholarly journals Highly diastereoselective synthesis of tricyclic fused-pyrans by sequential hydride shift mediated double C(sp3)–H bond functionalization

2018 ◽  
Vol 9 (37) ◽  
pp. 7327-7331 ◽  
Author(s):  
Keiji Mori ◽  
Nobuaki Umehara ◽  
Takahiko Akiyama
Keyword(s):  
Bronsted Acid ◽  
Brønsted Acid ◽  
Diastereoselective Synthesis ◽  
Bond Functionalization ◽  
Hydride Shift ◽  
Brönsted Acid ◽  
Acid Catalyzed

Highly diastereoselective synthesis of tricyclic fused-pyrans was achieved by Brønsted acid catalyzed double C(sp3)–H bond functionalization.

Brønsted Acid Catalysis: Hydrogen Bonding versus Ion Pairing in Imine Activation

2011 ◽  
Vol 50 (28) ◽  
pp. 6364-6369 ◽  
Author(s):  
Matthias Fleischmann ◽  
Diana Drettwan ◽  
Erli Sugiono ◽  
Magnus Rueping ◽  
Ruth M. Gschwind
Keyword(s):  
Hydrogen Bonding ◽  
Acid Catalysis ◽  
Ion Pairing ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Brönsted Acid ◽  
Bronsted Acid Catalysis
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