Chemoselectivity of the CuAAC/Ring Cleavage/Cyclization Reaction between Enaminones and α-Acylketenimine DOI

Guanrong Li,

Danyang Luo,

Qiaoli Luo

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(4), P. 2190 - 2199

Published: Jan. 27, 2024

Ketenimines represent an important class of reactive species, useful synthetic intermediates, and synthons. However, in general, ketenimines preferentially undergoes nucleophilic addition reactions with hydroxyl amino groups, carbon functional groups remain a less studied subset such systems. Herein, we develop straightforward syntheses pyridin-4(1H)-imines that is achieved by cyclization reacting enaminone unit α-acylketenimine which generated from the sulfonyl azides terminal ynones situ (CuAAC/Ring cleavage reaction). The cascade process starts α-C instead group, attacking electron-deficient central ketenimine, chemoselectivity unconventional products were formed intramolecular cyclization.

Language: Английский

Chiral Brønsted acid-catalyzed asymmetric intermolecular [4 + 2] annulation of ynamides with para-quinone methides DOI

Hang‐Hao Li,

Ya-Nan Meng,

Can‐Ming Chen

et al.

Science China Chemistry, Journal Year: 2023, Volume and Issue: 66(5), P. 1467 - 1473

Published: April 12, 2023

Language: Английский

Citations

18
Lewis acid-catalyzed (3+2) annulation of bicyclobutanes with ynamides: Access to 2-amino bicyclo[2.1.1]hexenes DOI Creative Commons

Deeptanu Sarkar,

Shiksha Deswal,

Rohan Chandra Das

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Strain-release driven annulations with bicyclo[1.1.0]butanes (BCBs) have become an attractive area of research for the synthesis bioisosteric bicyclohexane derivatives, which play a vital role in drug discovery. Interestingly, utilization inherent strain BCBs functionalized amino-bicyclo[2.1.1]hexenes, may spatially mimic substituted benzenes and anilines, has received only scant attention. Herein, we report Sc(OTf)

Language: Английский

Citations

7
Brønsted acid-catalyzed asymmetric dearomatization of indolyl ynamides: Practical and enantioselective synthesis of polycyclic indolines DOI
Zhixin Zhang, Xuan Wang,

Jia‐Tian Jiang

et al.

Chinese Chemical Letters, Journal Year: 2022, Volume and Issue: 34(3), P. 107647 - 107647

Published: July 2, 2022

Language: Английский

Citations

24
Copper-catalyzed enantioselective diyne cyclizationviaC(sp2)–O bond cleavage DOI Creative Commons

Ji‐Jia Zhou,

Ya-Nan Meng,

Li‐Gao Liu

et al.

Chemical Science, Journal Year: 2023, Volume and Issue: 14(13), P. 3493 - 3500

Published: Jan. 1, 2023

A copper-catalyzed asymmetric cascade cyclization via C(sp 2 )–O bond cleavage is disclosed, affording a range of chromeno[3,4- c ]pyrroles bearing triaryl oxa-quaternary carbon stereocenter in high yields and enantioselectivities.

Language: Английский

Citations

14
Chemoselectivity of the CuAAC/Ring Cleavage/Cyclization Reaction between Enaminones and α-Acylketenimine DOI

Guanrong Li,

Danyang Luo,

Qiaoli Luo

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(4), P. 2190 - 2199

Published: Jan. 27, 2024

Ketenimines represent an important class of reactive species, useful synthetic intermediates, and synthons. However, in general, ketenimines preferentially undergoes nucleophilic addition reactions with hydroxyl amino groups, carbon functional groups remain a less studied subset such systems. Herein, we develop straightforward syntheses pyridin-4(1H)-imines that is achieved by cyclization reacting enaminone unit α-acylketenimine which generated from the sulfonyl azides terminal ynones situ (CuAAC/Ring cleavage reaction). The cascade process starts α-C instead group, attacking electron-deficient central ketenimine, chemoselectivity unconventional products were formed intramolecular cyclization.

Language: Английский

Citations

5