Organic Letters, Journal Year: 2022, Volume and Issue: 24(11), P. 2149 - 2154
Published: March 16, 2022
The diastereo- and enantioselective dearomative formal [3 + 2] cycloaddition of 2-nitrobenzofurans α-aryl-α-isocyanoacetate esters provides tricyclic compounds bearing the 3
Language: Английский
Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(5), P. 620 - 681
Published: Jan. 17, 2023
Abstract This review updates the field of enantioselective domino reactions promoted by chiral catalysts derived from noble metals, including palladium, silver, rhodium, ruthenium, iridium and gold, published since beginning 2019. It illustrates how much a diversity these allow unprecedented asymmetric many types to be achieved with excellent enantioselectivity, giving direct access wide variety complex molecules. magnified image
Language: Английский
Citations
22
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
Organic Letters, Journal Year: 2024, Volume and Issue: 26(15), P. 3310 - 3315
Published: April 8, 2024
A catalyst system consisting of a chiral phosphoramidite ligand and Pd2(dba)3·CHCl3 causes the decarboxylation 5-vinyloxazolidine-2,4-diones to generate amide-containing aza-π-allylpalladium 1,3-dipole intermediates, which are capable triggering dearomatization 3-nitroindoles for diastereo- enantioselective [3+2] cycloaddition, leading formation series highly functionalized pyrroloindolines containing three contiguous stereogenic centers with excellent results (up 99% yield, 88:12 dr, 96% ee).
Language: Английский
Citations
8
European Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown
Published: Jan. 2, 2025
Abstract This review collects the recent developments in synthesis of chiral heterocycles through enantioselective silver‐catalyzed transformations published since 2018. It demonstrates power silver catalysts as special mild Lewis acids to provide an impressive diversity reaction pathways, such 1,3‐dipolar cycloadditions, various types cyclizations, along with a wide variety more complex domino/tandem reactions, allowing many novel heterocyclic products be achieved high enantioselectivities.
Language: Английский
Citations
1
Organic Letters, Journal Year: 2025, Volume and Issue: unknown
Published: Feb. 8, 2025
We report the first example of dearomative (3 + 2) cycloadditions 3-nitro(aza)-indole, -benzofuran, and -benzothiophene derivatives in presence allenyl sulfones, using sulfinate ammonium ion pairs as organocatalytic promoters. The methodology provides a new, facile, efficient protocol for synthesis functionalized 2,3-fused cyclopentannulated indolines dihydrobenzofurans.
Language: Английский
Citations
1
Organic Letters, Journal Year: 2022, Volume and Issue: 24(45), P. 8348 - 8353
Published: Nov. 10, 2022
A palladium-catalyzed enantioselective α-allylation of deconjugated butenolides with aza-π-allylpalladium 1,4-diploes, in situ generated from palladium-mediated decarboxylation cyclic carbamates and amide-substituted acyclic carbonates, has been successfully developed. An array enantioenriched 2-piperidones bearing an all-carbon quaternary stereocenter were obtained high yields excellent enantioselectivities (up to 99% yield ee). The utility this method was also showcased by a large-scale reaction synthetic transformations the product.
Language: Английский
Citations
29
The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(9), P. 6025 - 6037
Published: April 18, 2022
A dearomatization process of 3-nitroindoles enabled using palladium-catalyzed decarboxylative [4 + 2] cycloaddition either 2-alkylidenetrimethylene carbonates or 2-(hydroxymethyl)-3-arylallyl has been developed, affording a wide range indoline-fused tetrahydropyrans in good yields with excellent diastereoselectivities. This reaction features substrate scope and mild conditions represents the first example application π-allyl palladium 1,4-[O,C]-dipole species for dearomative electron-deficient heteroarenes.
Language: Английский
Citations
27
Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(21), P. 4332 - 4357
Published: Jan. 1, 2023
Silver catalysis offers environmentally friendly and simple protocols to construct N-heterocycles. Inspired by its appeal, herein we have summarized developments in the silver-catalyzed synthesis of N-heterocycles since 2019.
Language: Английский
Citations
12
Chirality, Journal Year: 2022, Volume and Issue: 34(7), P. 1019 - 1034
Published: May 6, 2022
Abstract A readily available chiral cyclohexanediamine‐derived bifunctional tertiary amine‐squaramide catalyst is more effective for the asymmetric dearomative 1,3‐dipolar cycloaddition of 2‐nitrobenzofurans and N ‐2,2,2‐trifluoroethylisatin ketimines. range structurally diverse spiro‐fused polyheterocyclic compounds containing oxindole, pyrrolidine, hydrobenzofuran motifs were smoothly obtained in excellent results (up to 99% yield, >20:1 dr all cases up ee). This method features high efficiency, mild reaction conditions, exquisite induction, wide functional group tolerance, great potential scale‐up synthesis, attractive product diversification.
Language: Английский
Citations
17
Organic Letters, Journal Year: 2024, Volume and Issue: 26(13), P. 2623 - 2628
Published: March 24, 2024
An efficient dearomative cyclization of 2-nitrobenzofurans via a thiol-triggered tandem Michael addition/intramolecular Henry reaction has been developed. A range thiochromeno[3,2-b]benzofuran-11-ols and tetrahydrothieno[3,2-b]benzofuran-3-ols could be obtained in up to 99% yield >20:1 dr. The valuable thiochromone fused benzofurans prepared with the 2-mercaptobenzaldehyde reaction/rearomatization/oxidative dehydrogenation process one-pot two-step operation. mechanism for was tentatively proposed.
Language: Английский
Citations
4