Palladium-Catalyzed Cycloaddition Reactions of π–Allylpalladium 1,4-Dipoles with 1,3,5-Triazinanes: Access to Hexahydropyrimidines, 1,3-Oxazinanes, and 1,5-Diazocanes DOI
Xinhua Zhang,

Zhi‐Hui Wang,

Yan Chen

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 8363 - 8375

Published: June 7, 2024

Palladium-catalyzed decarboxylation of 5-methylene-1,3-oxazinan-2-ones and 5-methylene-1,3-dioxan-2-ones to generate aza-π-allylpalladium oxa-π-allylpalladium 1,4-dipoles for [4 + 2] cycloaddition reaction with 1,3,5-triazinanes was developed, affording a wide range hexahydropyrimidine 1,3-oxazinane derivatives in good excellent yields (up 99%). The acyclic sulfonamido-substituted allylic carbonates as 1,4-dipole precursors also apply the developed synthesized strategy, achieving synthesis hexahydropyrimidines. Moreover, situ-generated undergoing dimeric 4] were demonstrated by construction 1,5-diazocane derivatives.

Language: Английский

B(C6F5)3/Chiral Phosphoric Acid Catalyzed Asymmetric Aza-Diels–Alder Reaction of Imines and Unactivated Dienes DOI
Zhen Liu,

Qing-Chun Qian,

Liming Chen

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(15), P. 3247 - 3251

Published: April 1, 2024

Herein, we report an asymmetric aza-Diels–Alder reaction of quinoxalinones or benzoxazinones with unactivated dienes by utilizing a B(C6F5)3/chiral phosphoric acid catalyst to construct chiral six-membered N-heterocycles. Various electron-withdrawing and electron-donating groups were tolerated (up 99% yield ee) in the methodology only 2 mol % loading. Moreover, luminescence mechanism photophysical properties product tested used for anticounterfeiting QR codes.

Language: Английский

Citations

2
Aza-[4 + 2] annulations of α-vinyl Morita–Baylis–Hillman adducts for regiodivergent synthesis of exomethylene-bearing azatricyclic compounds DOI
Ye Liu,

Chao-Xu Li,

Huang Chen

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(12), P. 3415 - 3420

Published: Jan. 1, 2024

The regiodivergent synthesis of exomethylene-bearing azatricyclic products was achieved via aza-[4 + 2] annulations cyclic imines with a single C4 synthon, the α-vinyl MBH adduct.

Language: Английский

Citations

0
Palladium-Catalyzed Cycloaddition Reactions of π–Allylpalladium 1,4-Dipoles with 1,3,5-Triazinanes: Access to Hexahydropyrimidines, 1,3-Oxazinanes, and 1,5-Diazocanes DOI
Xinhua Zhang,

Zhi‐Hui Wang,

Yan Chen

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 8363 - 8375

Published: June 7, 2024

Palladium-catalyzed decarboxylation of 5-methylene-1,3-oxazinan-2-ones and 5-methylene-1,3-dioxan-2-ones to generate aza-π-allylpalladium oxa-π-allylpalladium 1,4-dipoles for [4 + 2] cycloaddition reaction with 1,3,5-triazinanes was developed, affording a wide range hexahydropyrimidine 1,3-oxazinane derivatives in good excellent yields (up 99%). The acyclic sulfonamido-substituted allylic carbonates as 1,4-dipole precursors also apply the developed synthesized strategy, achieving synthesis hexahydropyrimidines. Moreover, situ-generated undergoing dimeric 4] were demonstrated by construction 1,5-diazocane derivatives.

Language: Английский

Citations

0