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

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




2016 ◽  
Vol 14 (24) ◽  
pp. 5525-5528 ◽  
Author(s):  
T. Beisel ◽  
J. Kirchner ◽  
T. Kaehler ◽  
J. Knauer ◽  
Y. Soltani ◽  
...  

A Brønsted acid-catalyzed addition of 2-alkylazaarenes to in situ generated N-sulfonylimines through selective C(sp3)–H bond functionalization has been developed.



Synthesis ◽  
2017 ◽  
Vol 50 (06) ◽  
pp. 1307-1314 ◽  
Author(s):  
Guang-Jian Mei ◽  
Zheng Cao ◽  
Gui-Xiang Zhou ◽  
Chun Ma ◽  
Kang Jiang

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.



Author(s):  
Valentina Marras ◽  
Pierluigi Caboni ◽  
Francesco Secci ◽  
Régis Guillot ◽  
David J. Aitken ◽  
...  

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.







Author(s):  
Mizzanoor Rahaman ◽  
M. Shahnawaz Ali ◽  
Khorshada Jahan ◽  
Damon Hinz ◽  
Jawad Bin Belayet ◽  
...  


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