High diastereoselective synthesis of spiro-isoxazolonechromans via domino oxa-Michael/1,6-addition reactions of ortho-hydroxyphenylsubstituted para-quinone methides with unsaturated isoxazolones

Tetrahedron ◽  
2019 ◽  
Vol 75 (5) ◽  
pp. 682-687 ◽  
Author(s):  
Zaijun Ye ◽  
Lijuan Bai ◽  
Yan Bai ◽  
Zongjie Gan ◽  
Hui Zhou ◽  
...  
Keyword(s):  
Addition Reactions ◽  
Diastereoselective Synthesis ◽  
Quinone Methides

scholarly journals Cover Feature: para -Quinone Methides as Acceptors in 1,6-Nucleophilic Conjugate Addition Reactions for the Synthesis of Structurally Diverse Molecules (Eur. J. Org. Chem. 18/2020)

2020 ◽  
Vol 2020 (18) ◽  
pp. 2642-2642
Author(s):  
Carolina G. S. Lima ◽  
Fernanda P. Pauli ◽  
Dora C. S. Costa ◽  
Acácio S. de Souza ◽  
Luana S. M. Forezi ◽  
...  
Keyword(s):  
Conjugate Addition ◽  
Addition Reactions ◽  
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.

Sign in / Sign up

Export Citation Format

Share Document