Journal of Molecular Structure, Journal Year: 2024, Volume and Issue: unknown, P. 141010 - 141010
Published: Dec. 1, 2024
Language: Английский
ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 5796 - 5805
Published: March 25, 2025
The transition metal-catalyzed asymmetric [n + 2] cycloaddition reaction with oxy-substituted ketene intermediates remains a synthetic challenge due to the limited availability of suitable precursors. Herein, we report visible-light-driven, palladium-catalyzed [4 vinyl benzoxazinanones siloxyketene intermediates, generating structurally diverse chiral quinolinone derivatives satisfactory diastereo- and enantioselectivities. transient generation siloxyketenes from α-ketoacylsilylanes through visible-light-induced Brook rearrangement is important for success present cycloaddition. 13C-labeling experiments reveal pathway involving [1,3]-silyl migration process. side arm effects BOX ligand silyl steric hindrance α-ketoacylsilanes play crucial roles in stereoselectivity control, theoretical calculations provide insights into stereochemical outcome reaction.
Language: Английский
Citations
1
Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 22(1), P. 37 - 54
Published: Nov. 27, 2023
Developing efficient and straightforward strategies to rapidly construct structurally distinct diverse organic molecules is one of the most fundamental tasks in synthesis, drug discovery materials science. In recent years, divergent synthesis functional from same starting has attracted significant attention been recognized as an powerful strategy. To achieve this objective, proper adjustment reaction conditions, such catalysts, solvents, ligands, etc., required. review, we summarized efforts chemo-, regio- stereodivergent reactions involving acyclic cyclic systems catalyzed by palladium complexes. Meanwhile, types, including carbonylative reactions, coupling cycloaddition well probable mechanism have also highlighted detail.
Language: Английский
Citations
14
Advanced Science, Journal Year: 2024, Volume and Issue: 11(31)
Published: June 17, 2024
Abstract Oxazocines are key structural intermediates in the synthesis of natural products and pharmaceutical molecules. However, oxazocines especially a highly enantioselective manner, is long‐standing formidable challenge due to unfavorable energetics involved cyclization. Herein, series new PNP‐Ligand P ‐chiral stereocenter first designed synthesized, called MQ‐Phos , successfully applied it Pd‐catalyzed higher‐order formal [4+4]‐cycloaddition α β ‐unsaturated imines with 2‐(hydroxymethyl)‐1‐arylallyl carbonates. The reaction features mild conditions, excellent regio‐ enantiocontrol broad substrate scope (54 examples). Various medium‐sized rings can be afforded moderate yields (up 92%) enantioselectivity 99% ee). newly developed critical for ring catalytic reactivity enantioselectivity.
Language: Английский
Citations
6
Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(31), P. 6342 - 6351
Published: Jan. 1, 2024
A facile strategy for the synthesis of valuable indolines has been developed, involving a palladium(II)/Brønsted acid co-catalyzed annulation readily available (2-aminophenyl)methanols and sulfoxonium ylides. This protocol allows direct utilization OH group as leaving group, tolerates alkyl aryl groups on N atom aniline moiety, operates under mild reaction conditions, exhibits good efficiency.
Language: Английский
Citations
1
Catalysts, Journal Year: 2024, Volume and Issue: 14(8), P. 508 - 508
Published: Aug. 6, 2024
We reported palladium-catalyzed regioselective [3+2] cycloadditions of α,β-unsaturated imines with vinylethylene carbonates, providing the desired oxazolidines in moderate-to-high yields. This reaction provides a facile route for highly synthesis functional oxazolidines. The synthetic utility current method was also demonstrated by gram-scale reaction.
Language: Английский
Citations
0
Organic Letters, Journal Year: 2024, Volume and Issue: unknown
Published: Sept. 30, 2024
Macrolactones are commonly found in natural products and pharmaceuticals. Herein, we present Pd-catalyzed [7 + 5] higher-order annulations between unprecedented oxa-1,n-dipoles (n = 7-9) with active enol lactones. This protocol enables the rapid synthesis of complex 12 to 15-membered lactones bearing internal
Language: Английский
Citations
0
Synthesis, Journal Year: 2024, Volume and Issue: 56(24), P. 3870 - 3878
Published: Oct. 7, 2024
Abstract The development of new catalytic systems that enable regio- and chemoselective construction diversely functionalized oxazocines is an important topic in organic synthesis pharmacochemistry. Herein, a novel Pd/Mengphos complex was designed applied palladium-catalyzed high-order [4+4] cycloaddition 2-substituted allylic carbonates to α,β-unsaturated imines, allowing facile access versatile good yields with excellent b/l Z/E selectivities (up 92% yield complete selectivities). reaction exhibited broad substrate scope, mild conditions, functional group compatibility. In addition, asymmetric version has also been tested, affording the desired moderate enantioselectivity.
Language: Английский
Citations
0
Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown
Published: Oct. 16, 2024
Abstract Six‐membered endocyclic benzyl/allyl enecarbamates undergo a Pd‐catalyzed decarboxylation process to generate 1‐azaallyl anions and Pd–benzyl/allyl cations. The ion pair then react with each other followed by reduction ultimately give unprotected 2‐(hetero)aryl‐3‐benzylpiperidines 2‐(hetero)aryl‐3‐allylpiperidines in 31–91% yields as single cis ‐diastereomers. These reactions represent strategy form β ‐substituted piperidines, which generates elusive anion intermediates introducing the negative charge from N‐terminal.
Language: Английский
Citations
0
Journal of Molecular Structure, Journal Year: 2024, Volume and Issue: unknown, P. 141010 - 141010
Published: Dec. 1, 2024
Language: Английский
Citations
0