Reactions of o-Quinone Methides with Pyridinium Methylides: A Diastereoselective Synthesis of 1,2-Dihydronaphtho[2,1-b]furans and 2,3-Dihydrobenzofurans

2013 ◽  
Vol 78 (11) ◽  
pp. 5505-5520 ◽  
Author(s):  
Vitaly A. Osyanin ◽  
Dmitry V. Osipov ◽  
Yuri N. Klimochkin
Keyword(s):  
Diastereoselective Synthesis ◽  
Quinone Methides

Diastereoselective Synthesis of Tetrahydroquinolines via [4 + 2] Annulation between in Situ Generated p-Quinone Methides and Nitroalkenes

2018 ◽  
Vol 20 (19) ◽  
pp. 5995-5998 ◽  
Author(s):  
Junwei Wang ◽  
Xiang Pan ◽  
Jian Liu ◽  
Lin Zhao ◽  
Ying Zhi ◽  
...  
Keyword(s):  
Diastereoselective Synthesis ◽  
Quinone Methides

Diastereoselective Synthesis of Tetrahydroquinolines Bearing Oxindole Scaffolds via Annulation of in Situ Generated p ‐Quinone Methides

2020 ◽  
Vol 362 (13) ◽  
pp. 2755-2759 ◽  
Author(s):  
Junwei Wang ◽  
Lei Zhao ◽  
Lin Zhao ◽  
Xiang Pan ◽  
Cheng Lv ◽  
...  
Keyword(s):  
Diastereoselective Synthesis ◽  
Quinone Methides

scholarly journals Diastereoselective synthesis of CF3-dihydrobenzofurans by [4+1] annulation of in situ-generated CF3-o-quinone methides and sulfur ylides

RSC Advances ◽  
2020 ◽  
Vol 10 (63) ◽  
pp. 38588-38591
Author(s):  
Babli K. Jha ◽  
Jaggaraju Prudhviraj ◽  
Prathama S. Mainkar ◽  
Nagender Punna ◽  
Srivari Chandrasekhar
Keyword(s):  
Diastereoselective Synthesis ◽  
Quinone Methides ◽  
Reaction Conditions ◽  
Sulfur Ylides

The first [4 + 1] annulation reaction of in situ-generated highly electrophilic CF3-ortho-quinone methides with sulphur ylides has been put forth under mild reaction conditions to access CF3-dihydrobenzofurans.

scholarly journals Highly Diastereoselective Synthesis of Tetrahydroquinoline Derivatives via [4 + 2] Annulation of Ortho-Tosylaminophenyl-Substituted Para-Quinone Methides and Cyanoalkenes

2021 ◽  
Vol 9 ◽  
Author(s):  
Taiwei Dong ◽  
Peifeng Wei ◽  
Min Li ◽  
Feng Gao ◽  
Yuan Qin
Keyword(s):  
Biologically Active ◽  
Structural Motif ◽  
Diastereoselective Synthesis ◽  
Atom Economy ◽  
Quinone Methides ◽  
One Pot ◽  
Reaction Performance ◽  
High Yields ◽  
Active Natural

As a privileged structural motif, tetrahydroquinoline skeletons widely exist in biologically active natural products and pharmaceuticals. In this protocol, a highly diastereoselective [4 + 2] annulation of ortho-tosylaminophenyl-substituted p-QMs and cyanoalkenes to construct tetrahydroquinoline derivatives has been successfully achieved. This strategy proceeds efficiently under mild condition, offering straightforward route to a variety of 4-aryl-substituted tetrahydroquinolines with high yields, excellent diastereoselectivities, broad functional group tolerance as well as gram-scale capacity. Moreover, a one-pot reaction sequence utilizing in situ generated p-QMs under the similar condition to build tetrahydroquinoline framework is smoothly conducted with good reaction performance as well as step and atom economy.

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.

P(NMe2)3-Mediated Umpolung Spirocyclopropanation Reaction of p-Quinone Methides: Diastereoselective Synthesis of Spirocyclopropane-Cyclohexadienones

2020 ◽  
Vol 22 (21) ◽  
pp. 8376-8381
Author(s):  
Yu-Hua Deng ◽  
Wen-Dao Chu ◽  
Yun-Han Shang ◽  
Ke-Yin Yu ◽  
Zhi-Long Jia ◽  
...  
Keyword(s):  
Diastereoselective Synthesis ◽  
Quinone Methides
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