Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: unknown
Published: Nov. 13, 2024
An amine-catalyzed atroposelective FC alkylation of 2-arylindoles with α,β-unsaturated aldehydes via the DKR process has been developed. Various axially chiral were obtained in good yields high enantioselectivities.
Language: Английский
Science Advances, Journal Year: 2024, Volume and Issue: 10(19)
Published: May 10, 2024
Atropisomeric indoles defined by a N─N axis are an important class of heterocycles in synthetic and medicinal chemistry material sciences. However, they remain heavily underexplored due to limited methods challenging stereocontrol over the short bonds. Here, we report highly atroposelective access axially chiral via asymmetric Larock reaction. This protocol leveraged powerful role phosphoramidite ligand attenuate common dissociation original reaction, forming with excellent functional group tolerance high enantioselectivity palladium-catalyzed intermolecular annulation between readily available o -iodoaniline alkynes. The multifunctionality prepared allowed diverse post-coupling transformations, affording broad array functionalized indoles. Experimental computational studies have been conducted explore reaction mechanism, elucidating enantio-determining rate-limiting steps.
Language: Английский
Citations
8
Molecular Catalysis, Journal Year: 2024, Volume and Issue: 560, P. 114150 - 114150
Published: April 16, 2024
Language: Английский
Citations
3
ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(17), P. 13055 - 13064
Published: Aug. 15, 2024
Catalytic asymmetric hydrofunctionalization of π-bonds has been extensively studied, but the alkynes that affords atropoisometric products remains heavily underexplored. We herein report [Rh(COD)OAc]2/Mg(NTf2)2-catayzed highly atroposelective hydroselenation two classes 1-alkynylindoles using selenophenols, where Mg(II) salt both activates Rh catalyst and provides a key NTf2 anion essential for catalytic activity enantioselectivity, affording C–N axially chiral trisubstituted olefins bear relatively low racemization barrier (ΔG‡ ∼ 27 kcal/mol). The system features high activity, mild reaction conditions, good functional group tolerance, regio-, (E)-, enantioselectivity. selenoether moiety in product framework can be readily functionalized to give synthetically useful products.
Language: Английский
Citations
3
The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 12559 - 12575
Published: Aug. 27, 2024
The catalytic atroposelective synthesis of N–N axially chiral indolylamides was established via dynamic kinetic resolution, which makes use Lewis base-catalyzed asymmetric acylation N-acylaminoindoles as a new type platform molecule with anhydrides. By this strategy, series were synthesized in overall good yields (up to 98%) excellent enantioselectivities 99% ee). Moreover, some these display extent anticancer activity, demonstrates their potential application medicinal chemistry. Therefore, work has not only provided strategy for the monoaryl indoles but also offered member configurational stability and promising application, thereby solving challenges indoles.
Language: Английский
Citations
2
Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(7), P. 2002 - 2007
Published: Jan. 1, 2024
An efficient method has been disclosed for the highly enantioselective synthesis of optically pure heptacyclic dihydronaphthofuran-fused indolo[2,1- b ]quinazoline derivatives.
Language: Английский
Citations
0
Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(49)
Published: June 26, 2024
Vinylidene ortho-quinone methides (VQMs) have been proven to be versatile and crucial intermediates in the catalytic asymmetric reaction last decade, thus drawn considerable concentrations on account of practical application construction enantiomerically pure functional organic molecules. However, comparison well established chiral Brønsted base-catalyzed via VQMs, acid-catalyzed is rarely studied there no systematic summary date. In this review, we summarize recent advances VQMs according three types reactions: a) intermolecular nucleophilic addition VQMs; b) cycloaddition c) intramolecular cyclization VQMs. Finally, put forward remained challenges opportunities for potential breakthroughs area.
Language: Английский
Citations
0
Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(21), P. 3718 - 3723
Published: Sept. 20, 2023
Abstract A Brønsted acid‐catalyzed dearomative skeletal rearrangement of azofurans with indoles is reported, enabling a regioselective 1,6‐addition, ring‐opening and 1,4‐addition cascade to produce 26 examples indolylated pyrrol‐2‐ones cyclic tetrasubstituted stereocenter in 58–94% yields. This protocol demonstrates remarkable compatibility regarding different substitution patterns, featuring complete regioselectivity.
Language: Английский
Citations
1
Organic Letters, Journal Year: 2024, Volume and Issue: 26(31), P. 6586 - 6590
Published: July 30, 2024
A rhodium-catalyzed [4 + 2] cycloaddition of ynamines and 2-(cyanomethyl)phenylboronates has been developed, leading to efficient excellent regioselective synthesis valuable indole-linked aromatic compounds in a concise flexible approach. Interestingly, this strategy was successful the construction C···N axially chiral indoles with high enantiocontrol by introduction new phosphoramidite ligand (Xie-Phos).
Language: Английский
Citations
0
Science China Chemistry, Journal Year: 2024, Volume and Issue: unknown
Published: Sept. 9, 2024
Language: Английский
Citations
0
Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: unknown
Published: Nov. 13, 2024
An amine-catalyzed atroposelective FC alkylation of 2-arylindoles with α,β-unsaturated aldehydes via the DKR process has been developed. Various axially chiral were obtained in good yields high enantioselectivities.
Language: Английский
Citations
0