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

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

Palladium-Catalyzed (4 + 1) Annulation of 4-Vinylbenzodioxinones with Sulfur Ylides: Diastereoselective Synthesis of Dihydrobenzofuran Derivatives DOI
Yi Tang, Xiaojing Sun,

Yu Tan

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 8951 - 8959

Published: May 30, 2024

Palladium-catalyzed (4 + 1) annulation of 4-vinylbenzodioxinones with sulfur ylides has been developed to afford various dihydrobenzofuran derivatives in moderate high yields excellent diastereoselectivities. The scale-up reaction and further derivations the product worked well, demonstrating application potential current organic synthesis.

Language: Английский

Citations

1

A palladium-catalyzed decarboxylative (5 + 5) cyclization reaction of vinyloxazolidine-2,4-diones: access to ten-membered N,O-containing heterocycles DOI
Xiaohui Fu, Juan Liao, Zhen‐Hua Wang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(15), P. 4131 - 4137

Published: Jan. 1, 2024

A palladium-catalyzed decarboxylative (5 + 5) cyclization reaction of vinyloxazolidine-2,4-diones for the synthesis ten-membered N,O-containing heterocycles is disclosed.

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