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

Palladium-Catalyzed Ligand-Directed Divergent Decarboxylative Cycloadditions of Vinyloxazolidine-2,4-diones with 1,3,5-Triazinanes DOI
Zhen‐Hua Wang, Xiaohui Fu, Qun Li

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(8), P. 1589 - 1594

Published: Feb. 22, 2024

This study demonstrates a highly efficient regiodivergent ligand-controlled palladium-catalyzed cycloaddition reaction of vinyloxazolidine-2,4-diones with 1,3,5-triazinanes. In the presence diphosphine ligand, proceeds via (5+2) pathway to afford 1,3-diazepin-4-ones in excellent yields, while using monophosphine smoothly (3+2) give imidazolidin-4-ones good yields.

Language: Английский

Citations

9
Palladium-catalyzed enantioselective decarboxylative allylic alkylation of α-benzyl cyanoacetates: access to chiral acyclic quaternary carbon stereocenters DOI
Qing Bao,

Ting-Jia Sun,

Yanping Zhang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(23), P. 5971 - 5977

Published: Jan. 1, 2023

A palladium-catalyzed enantioselective decarboxylative allylic alkylation of α-benzyl cyanoacetates with methylene cyclic carbamates was developed for the construction nitrile-containing acyclic quaternary carbon stereocenters good results.

Language: Английский

Citations

10
Pd-Catalyzed [4 + 1] Annulation Strategy to Functionalized 4-Methyleneproline Derivatives DOI Creative Commons
Jiaxin Han,

Wenzheng Gao,

Joseph P. A. Harrity

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(3), P. 1552 - 1555

Published: Jan. 23, 2024

A Pd-catalyzed formal [4 + 1] cycloaddition reaction of sulfur ylides and in situ-generated Pd-stabilized zwitterions offers a convenient route to series functionalized proline derivatives. The utility this method is demonstrated by gram-scale synthesis chemoselective functionalization proline-based derivative.

Language: Английский

Citations

3
A Pd‐Catalyzed Annulation Strategy to Linearly Fused Functionalized N‐Heterocycles DOI Creative Commons
Larry Hoteite, Benjamin D. W. Allen,

Ms. Ergaiya A. Elhajj

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(21)

Published: Feb. 7, 2024

Linearly fused polycyclic piperidines represent common substructures in natural products and biologically active small molecules. We have devised a Pd-catalyzed annulation strategy to these compounds that converts readily available 2-tetralones indanones into scaffolds with the potential for control of both enantio- diastereoselectivity. Importantly, can be chemoselectively functionalized, providing an efficient robust methodology important nitrogen-containing

Language: Английский

Citations

1
Catalyst-Free Ring Opening of Azlactones in Water Microdroplets† DOI
Kumar Naveen,

Vishesh Singh Rawat,

Rahul Verma

et al.

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

Published: Jan. 1, 2024

A catalyst-free method was developed for the ring opening of azlactones (also known as oxazolones) in water microdroplets.

Language: Английский

Citations

1
Cooperative Chiral Lewis Base/Palladium‐Catalyzed Asymmetric Syntheses of Methylene‐Containing δ‐Lactams DOI Creative Commons
Paul Zebrowski, Uwe Monkowius, Mario Waser

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(45)

Published: Oct. 19, 2023

We herein report a two-step approach for the enantioselective synthesis of novel chiral δ-lactams. By using cooperative ITU/achiral Pd-catalyst system, this protocol proceeds via an asymmetric α-allylation activated aryl esters first, followed by acid-mediated lactam formation. A variety differently substituted products could be obtained with usually high levels enantioselectivities and in reasonable yields (16 examples, up to 98 : 2 er 73 % yield over two steps). In addition, further utilizations transformations exocyclic double bond were successfully carried out as well.

Language: Английский

Citations

2
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