RSC Advances, Journal Year: 2023, Volume and Issue: 13(7), P. 4782 - 4786
Published: Jan. 1, 2023
The β,γ-positions of α,β-unsaturated ketones were reacted with ketoamides, the hydrogen amide as key factor to construct lactams.
Language: Английский
Chemical Science, Journal Year: 2023, Volume and Issue: 14(11), P. 3024 - 3029
Published: Jan. 1, 2023
Inspired by a fungicide, we designed 5-vinyloxazolidine-2,4-diones as new precursors of π-allylpalladium zwitterionic intermediates and developed palladium-catalyzed asymmetric (5 + 3) cycloaddition with azomethine imines (3 2) 1,1-dicyanoalkenes. Both reactions proceeded smoothly under mild reaction conditions to produce various chiral heterocyclic compounds in high yields excellent enantioselectivities. These results revealed that were type suitable precursor for palladium catalysis will find extensive applications Pd-catalyzed such allylic alkylation.
Language: Английский
Citations
27
Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: unknown
Published: Sept. 18, 2024
A Pd-catalyzed asymmetric higher-order dipolar cycloaddition between allenyl carbonates and azadienes is achieved by exploiting novel alkylidene-π-allyl-Pd dipoles. This research provides a modular platform for the synthesis of challenging chiral endocyclic allenes bearing medium-sized heterocyclic motif centrally stereocenter in good yields with high enantio- diastereoselectivities (29 examples, up to 97% yield, 97:3 er >19:1 dr). Experimental computational studies elucidate possible reaction mechanism observed stereochemical results. Based on mechanistic understanding, new π-propargyl-Pd dipole was designed further extend success higher order strategy 10-membered alkynes from propargyl (13 98% yield 94.5:5.5 er).
Language: Английский
Citations
11
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
The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown
Published: Oct. 4, 2024
A palladium-catalyzed regioselective [8 + 3] cycloaddition of tropsulfimides and tropones with vinylidenecyclopropane-diesters (VDCP-diesters) has been disclosed in this paper, affording decahydro-1
Language: Английский
Citations
5
Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(12), P. 2060 - 2066
Published: May 5, 2022
Abstract A palladium‐catalyzed [4+2] cycloaddition of hydroxy‐tethered allyl carbonates with five types electron‐deficient alkenes has been achieved, in which a type new acted as valuable precursors for the formation 1,4‐C,O‐dipole allylpalladium intermediates. The reaction proceeded efficiently under mild conditions to provide corresponding tetrahydropyran derivatives moderate high yields excellent diastereoselectivities. magnified image
Language: Английский
Citations
21
Organic Letters, Journal Year: 2023, Volume and Issue: 25(34), P. 6328 - 6333
Published: Aug. 23, 2023
The 5-allenyloxazolidine-2,4-diones had been synthesized as novel precursors of π-allyl palladium zwitterion and were applied in a palladium-catalyzed enantioselective (3 + 2) annulation by using barbiturate-derived alkenes the reaction partner presence an axially chiral phosphoramidite ligand. This proceeded smoothly under mild conditions, affording highly functionalized spirobarbiturate-γ-lactam derivatives excellent yields along with high diastereo- enantioselectivities. scale-up further transformation product also successful.
Language: Английский
Citations
12
Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(22), P. 3967 - 3972
Published: Oct. 18, 2022
Abstract In this paper, we designed and synthesized 4‐vinyl‐4‐butyrolactone as a precursor to generate the zwitterionic allylpalladium intermediates, which behaved five‐membered all‐carbon synthon in palladium‐catalyzed (5+3) annulation with azomethine imines, giving eight‐membered ring‐fused heterocycles (26 examples, 49% 97% yield, >20:1 dr). magnified image
Language: Английский
Citations
19
Chemical Communications, Journal Year: 2022, Volume and Issue: 58(46), P. 6646 - 6649
Published: Jan. 1, 2022
In this paper, a new type of δ-vinylvalerolactone was designed and synthesized, used as precursor in Pd-catalyzed [6+3] cycloaddition with azomethine imines, leading to nine-membered 1,2-dinitrogen-containing heterocycles 77-98% yields >20 : 1 d.r. These ring-fused products were further transformed into unusual tetracyclic bridged-ring compounds without loss the diastereoselectivities.
Language: Английский
Citations
18
ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(19), P. 13043 - 13055
Published: Sept. 22, 2023
Rendering a common ligand scaffold anionic and then pairing it with chiral cation represents an alternative strategy for developing enantioselective versions of challenging transformations, as has been recently demonstrated in the borylation arenes using quinine-derived cation. A significant barrier to further generalization this approach is lack understanding specific interactions involved between cation, ligand, substrate, given complexity system. We have embarked on detailed computational study probing mechanism, key noncovalent involved, potential origin selectivity desymmetrizing two distinct classes substrate. describe deconstructive, stepwise tackling complex challenge, which involves building up pairwise components nominally three component system before combining together into full 263-atom reactive complex. This revealed substantial differences occurring at stereodetermining transition state C-H oxidative addition iridium substrate classes. Each engages unique mixture diverse interactions, testament rich privileged structure cinchona alkaloid-derived cations. Throughout study, experimental support provided, culminates discovery that prochiral phosphine oxide substrates, lacking hydrogen bond donor functionality, can also give very encouraging levels enantioselectivity, potentially through direct envisage findings will spur developments cations controllers asymmetric transition-metal catalysis.
Language: Английский
Citations
10
Organic Letters, Journal Year: 2025, Volume and Issue: unknown
Published: Feb. 17, 2025
A cooperative palladium/chiral amine enabled diastereo- and enantioselective [3 + 2] cycloaddition of π-allyl 1,3-dipoles with α,β-unsaturated aldehydes has been developed. series highly functionalized cyclopentanes bearing three continuous tertiary stereocenters can be facilely efficiently obtained in good to excellent yields (51-97%) synthetically useful enantioselectivity (93-99% ee) under mild reaction conditions. Control experiments HRMS analyses were conducted elucidate the possible mechanism. The utility current method was demonstrated by gram-scale synthesis elaboration products into various cyclopentanes.
Language: Английский
Citations
0