A Brønsted acid catalyzed tandem reaction for the diastereoselective synthesis of cyclobuta-fused tetrahydroquinoline carboxylic esters

2021 ◽  
Author(s):  
Valentina Marras ◽  
Pierluigi Caboni ◽  
Francesco Secci ◽  
Régis Guillot ◽  
David J. Aitken ◽  
...  
Keyword(s):  
Michael Addition ◽  
Tandem Reaction ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Diastereoselective Synthesis ◽  
Cyclization Process ◽  
Brönsted Acid ◽  
Acid Catalyzed ◽  
Carboxylic Esters

We have established a Brønsted acid catalyzed diastereoselective synthesis of diversely substituted cyclobuta-fused tetrahydroquinoline carboxylic esters through a new tandem aza-Michael addition-aza-Friedel–Crafts cyclization process.

Solvent-free Brønsted acid-catalyzed Michael addition of nitrogen- and carbon-containing nucleophiles by ultrasound activation

2014 ◽  
Vol 55 (5) ◽  
pp. 1002-1005 ◽  
Author(s):  
Xiu-Jiang Du ◽  
Zhi-Peng Wang ◽  
Yan-Ling Hou ◽  
Cheng Zhang ◽  
Zheng-Ming Li ◽  
...  
Keyword(s):  
Michael Addition ◽  
Solvent Free ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Brönsted Acid ◽  
Acid Catalyzed ◽  
Ultrasound Activation

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.

Iodine mediated/Brønsted acid-catalyzed dimerization of vinylarenes: a tandem reaction through Ritter trapping to produce N-(4-iodo-1,3-diarylbutyl) acetamides

2012 ◽  
Vol 10 (18) ◽  
pp. 3610 ◽  
Author(s):  
Jing-Mei Huang ◽  
Zhi-Jun Ye ◽  
Dong-Song Chen ◽  
Hong Zhu
Keyword(s):  
Tandem Reaction ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Brönsted Acid ◽  
Acid Catalyzed

Asymmetric Brønsted Acid-catalyzed Intramolecular aza-Michael Reaction – Enantioselective Synthesis of Dihydroquinolinones

2012 ◽  
Vol 67 (10) ◽  
pp. 1021-1029 ◽  
Author(s):  
Magnus Rueping ◽  
Stefan A. Moreth ◽  
Michael Bolte
Keyword(s):  
Michael Addition ◽  
Heterocyclic Compounds ◽  
Michael Reaction ◽  
Biological Activities ◽  
Enantioselective Synthesis ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Brönsted Acid ◽  
Acid Catalyzed ◽  
High Yields

The enantioselective synthesis of 2-aryl-substituted 2,3-dihydroquinolin-4-ones, a class of heterocyclic compounds with interesting biological activities, has been achieved through a Brønsted acidcatalyzed enantioselective intramolecular Michael addition. The products are available in moderate to high yields and with good enantioselectivities.

Brønsted Acid-Catalyzed Propargylation/Cycloisomerization Tandem Reaction: One-Pot Synthesis of Substituted Oxazoles from Propargylic Alcohols and Amides

2009 ◽  
Vol 74 (8) ◽  
pp. 3148-3151 ◽  
Author(s):  
Ying-ming Pan ◽  
Fei-jian Zheng ◽  
Hai-xin Lin ◽  
Zhuang-ping Zhan
Keyword(s):  
Tandem Reaction ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
One Pot ◽  
Propargylic Alcohols ◽  
One Pot Synthesis ◽  
Brönsted Acid ◽  
Acid Catalyzed

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.

A Brønsted Acid‐Catalyzed Michael Addition/Cyclization Sequence for the Diastereoselective Assembly of Chroman‐Bridged Polycyclic Isoindolinones

2018 ◽  
Vol 361 (3) ◽  
pp. 456-461 ◽  
Author(s):  
Shaojing Jin ◽  
Jia Guo ◽  
Dongmei Fang ◽  
Yongwei Huang ◽  
Qilin Wang ◽  
...  
Keyword(s):  
Michael Addition ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Brönsted Acid ◽  
Acid Catalyzed
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