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

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
Phen-2NO, a new C2-symmetric rigid-featured tetradentate ligand, and its application in the asymmetric alkylation reaction of indoles DOI

Zi‐Yue Chen,

Ke‐Lan Xu,

Xirui Wang

et al.

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(15), P. 6670 - 6675

Published: Jan. 1, 2024

A new class of C 2 -symmetric rigid-featured chiral phen ligands that provide the N , O -tetradentate coordination moiety and two additional -dioxides were rationally designed developed.

Language: Английский

Citations

3
Naphthyridine–2NO, a new C2-symmetric rigid tetradentate bimetallic ligand and its application in asymmetric Friedel–Crafts alkylation DOI
Pan Hu,

Ke‐Lan Xu,

Xirui Wang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(9), P. 2600 - 2606

Published: Jan. 1, 2024

The development of a series novel and easily accessed chiral naphthyridine-type binucleating ligands for asymmetric catalysis.

Language: Английский

Citations

3
Recent Advances in Palladium-Catalyzed [4 + n] Cycloaddition of Lactones, Benzoxazinanones, Allylic Carbonates, and Vinyloxetanes DOI
Mengyan Guo, Panke Zhang, Er‐Qing Li

et al.

Topics in Current Chemistry, Journal Year: 2023, Volume and Issue: 381(6)

Published: Nov. 3, 2023

Language: Английский

Citations

9
Design and Synthesis of Rigid‐Featured Tertiary Amine‐Derived C2‐Symmetric Chiral Furan‐N,N′‐dioxide Ligands DOI

Zi‐Yue Chen,

Pan Hu, Xirui Wang

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(42)

Published: Aug. 19, 2023

Abstract To expand the chemical space of chiral N ‐oxides and furan‐containing ligands, herein we designed synthesized a new class rigid‐featured tertiary amine‐derived C 2 ‐symmetric furan‐ , N′ ‐dioxide (Fu‐2NO) ligands from optically pure l ‐prolinamides/hydroxylprolinamides in operationally simple two steps up to 57 % overall yield. The newly developed Fu‐2NO possesses pyrroloimidazolone‐based as non‐flat walls, afforded opportunity for fine‐tuning ligand electronic conformational properties by judicious choice substituent nonligating nitrogen atom. More importantly, can tolerate air moisture such that no special handling is needed their storage, be applied Ni(II)‐catalyzed asymmetric Friedel‐Crafts alkylation reaction indole.

Language: Английский

Citations

7
Asymmetric Synthesis of Functionalizable Type II β-Turn-Inducing α-Amino Acid Building Blocks DOI Creative Commons

Wenzheng Gao,

Jiaxin Han,

Sophie Greaves

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(35), P. 6555 - 6559

Published: Aug. 29, 2023

Peptidomimetics are emerging as a promising class of potent and selective therapeutics. Among the current approaches to these compounds, utilization constrained lactams is key element in enforcing active peptide conformation, development efficient stereocontrolled methods for generating such lactam building blocks an important objective. Current typically rely on elaboration existing α-amino acids, so doing, side chain sacrificed during ring-forming process. We report new asymmetric approach lactam-constrained acid bearing range polar hydrophobic chains. The chemistry amenable rapidly di- tripeptides, potential stabilize type II β-turns demonstrated synthesis melanocyte-inhibiting factor peptidomimetic.

Language: Английский

Citations

7
Palladium-catalyzed decarboxylative α-allylation of thiazolidinones and azlactones with sulfonamido-substituted acyclic allylic carbonates DOI

Han-Wen Rao,

Tian-lan Zhao, Long Wang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(42), P. 8593 - 8602

Published: Jan. 1, 2023

A palladium-catalyzed decarboxylative α-allylation of thiazolidinones and azlactones with aza-π-allylpalladium zwitterionic intermediates, in situ generated from sulfonamido-substituted allylic carbonates, is successfully developed. This method allows the formation a series structurally diverse 5-alkylated 2-piperidones under mild conditions moderate to high yields (up 99% yield).

Language: Английский

Citations

7
Palladium-catalyzed enantioselective decarboxylation of vinyl cyclic carbamates: generation of amide-based aza-1,3-dipoles and application to asymmetric 1,3-dipolar cycloaddition DOI
Xiaohui Fu, Yanping Zhang, Juan Liao

et al.

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 35(12), P. 109688 - 109688

Published: March 1, 2024

Language: Английский

Citations

2
Progress in catalytic asymmetric α-functionalization of vinylogous nucleophilic species DOI
Zhen‐Hua Wang, Yong You, Jian‐Qiang Zhao

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(12), P. 3130 - 3168

Published: Jan. 1, 2023

This review summarizes a view of the advances in catalytic asymmetric α-functionalization vinylogous nucleophilic species, content which is categorized based on type donor.

Language: Английский

Citations

6
Palladium-Catalyzed Asymmetric [3＋4] Cycloadditions for the Construction of Cyclohepta[b]indoles DOI Open Access
Yi Wang, Jian Zhang, Yangzi Liu

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 43(8), P. 2864 - 2864

Published: Jan. 1, 2023

A Pd-catalyzed decarboxylation strategy for the efficient synthesis of cyclohepta [b]indoles in good yields with to excellent enantioselectivities and moderate diastereoselectivities is reported.In this procedure, viny indoloxazolidones were activated by Pd catalyst generate zwitterionic intermediates situ, which then trapped electro-deficient diene species via asymmetric [3＋4] cycloaddition process.

Language: Английский

Citations

5