Highly Diastereoselective Synthesis of Polycyclic Indolines through Formal [4+2] Propargylic Cycloaddition of Indoles with Ethynyl Benzoxazinanones.
@article{Shao2020HighlyDS, title={Highly Diastereoselective Synthesis of Polycyclic Indolines through Formal [4+2] Propargylic Cycloaddition of Indoles with Ethynyl Benzoxazinanones.}, author={W. L. Shao and Qing‐Feng Xu‐Xu and Shu‐Li You}, journal={Chemistry, an Asian journal}, year={2020} }
A formal [4+2] propargylic annulation of indoles and pyrrole with ethynyl benzoxazinanones was described. This protocol provides a concise synthesis of tetrahydro-5 H -indolo[2,3- b ]quinolines and tetrahydro-3 H -pyrrolo[3,2- b ]quinoline, the core structures of alkaloid frameworks, featuring excellent yields, high diastereoselectivity, mild conditions and wide substrate scope.
3 Citations
Synthesis of Heterobiaryl 4-Aryl Furans through a Base-Promoted Decarboxylative Propargylation/Cycloisomerization Annulation.
- Chemistry, BiologyOrganic letters
- 2020
A transition-metal-free synthesis of heterobiaryl 4-aryl furans through a base-promoted decarboxylative propargylation/cycloisomerization annulation of ethynyl benzoxazinanones and readily accessible…
Palladium-Catalyzed Intramolecular Diastereoselective Dearomatization Reaction of Indoles with N-Tosylhydrazones
- Chemistry, BiologyOrganic Chemistry Frontiers
- 2021
A novel highly diastereoselective palladium-catalyzed dearomative reaction of N-halobenzoyl o-haloaniline derivatives has been developed using functionalized N-tosylhydrazones as the coupling…
Recent Advances in Metal‐Catalyzed Decarboxylative Reactions of Vinyl Benzoxazinanones
- ChemistryAdvanced Synthesis & Catalysis
- 2021
References
SHOWING 1-10 OF 94 REFERENCES
Highly Diastereo- and Enantioselective Synthesis of Tetrahydro-5H-Indolo[2,3-b]quinolines through Copper-Catalyzed Propargylic Dearomatization of Indoles.
- Chemistry, BiologyChemistry
- 2017
The first copper-catalyzed intermolecular asymmetric propargylic dearomatization/annulation cascade sequence of indoles via a copper-allenylidene amphiphilic intermediate has been achieved. This…
Concise Synthesis of Polycyclic Indoline Scaffolds through an InIII-Catalyzed Formal [4+2] Annulation of 2,3-Disubstituted Indoles with o-Aminobenzyl Alcohols
- Chemistry
- 2017
A concise indium(III)-catalyzed annulation of 2,3-disubstituted indoles with o-aminobenzyl alcohols is reported. The in situ generated aza-ortho-quinone methides (aza-oQMs) were efficiently trapped…
Asymmetric Catalytic [4 + 2] Cycloaddition via Cu-Allenylidene Intermediate: Stereoselective Synthesis of Tetrahydroquinolines Fused with a γ-Lactone Moiety.
- Chemistry, BiologyOrganic letters
- 2018
The utility of this method was exemplified by the removal of the N-protecting groups and derivatization on the terminal alkyne functionality of the cyclization products.
Asymmetric [3 + 3] Annulation of Copper-Allenylidenes with Pyrazolones: Synthesis of Chiral 1,4-Dihydropyrano[2,3- c]pyrazoles.
- ChemistryOrganic letters
- 2018
The copper-catalyzed asymmetric [3 + 3] annulation of ethynyl benzoxazinanones with pyrazolones has been achieved, providing simple access to 1,4-dihydropyrano[2,3- c]pyrazole derivatives in moderate…
Diastereo- and enantioselective palladium-catalyzed dearomative [4 + 2] cycloaddition of 3-nitroindoles
- ChemistryChinese Chemical Letters
- 2019
Asymmetric [4+2] cycloaddition of azlactones with dipolar copper–allenylidene intermediates for chiral 3,4-dhydroquinolin-2-one derivatives
- ChemistryTetrahedron Letters
- 2019
Catalytic Asymmetric [4 + 3] Annulation of C, N-Cyclic Azomethine Imines with Copper Allenylidenes.
- Chemistry, BiologyOrganic letters
- 2018
The first asymmetric decarboxylative annulation of propargylic carbamates with C, N-cyclic azomethine imines has been developed successfully by a copper- N-heterocyclic carbine system and Cu-allenylidene intermediates play a crucial role in this transformation.
Construction of optically active indolines by formal [4+1] annulation of sulfur ylides and N-(ortho-chloromethyl)aryl amides.
- ChemistryChemistry
- 2013
The described strategy, taking advantage of chiral sulfur ylides, represents a direct procedure to access chiral 2-substituted indolines.
N-Heterocyclic Carbene/Copper Cooperatively Catalyzed Asymmetric Synthesis of Spirooxindoles.
- Chemistry, BiologyAngewandte Chemie
- 2019
Both reactions represent a nicely synergistic integration of NHC carbene and copper catalysis, in which each catalyst activates the substrates, respectively, and the chiral NHC perfectly controls the stereochemistry.
A concise construction of 4-alkynylquinazolines via [4 + 2] annulation of 4-alkynylbenzoxazinanones with acylhydroxamates under transition-metal-free conditions
- Chemistry, BiologyOrganic Chemistry Frontiers
- 2019
A concise and highly efficient method for the construction of valuable 4-alkynylquinazolines under transition-metal-free conditions was developed via [4 + 2] annulation of 4-alkynylbenzoxazinanones…