Rh(III)-Catalyzed Redox-Neutral [4+2] Annulation for Direct Assembly of 3-Acyl Isoquinolin-1(2H)-ones as Potent Antitumor Agents.
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DOI: 10.1002/cplu.201900616
Abstract: By virtue of an efficient rhodium(III)-catalyzed redox-neutral C-H activation/ring-opening of a strained ring/[4+2] annulation cascade of N-methoxybenzamides with propargyl cycloalkanols, diverse 3-acyl isoquinolin-1(2H)-ones were directly obtained in good yields and with excellent functional group compatibility.… read more here.
Keywords: annulation; iii catalyzed; redox neutral; isoquinolin ones ... See more keywords
Lewis Acid Catalyzed [3+3] Annulation of Donor–Acceptor Cyclopropanes with γ-Hydroxyenones: Access to Highly Functionalized Tetrahydropyrans
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DOI: 10.1002/ejoc.201601305
Abstract: Donor–acceptor cyclopropanes were engaged in a [3+3]-annulation reaction with γ-hydroxyenones. Sc(OTf)3 was found to be the best catalyst, and 2,4,4,5-tetrasubstituted tetrahydropyran products were obtained in good yields under mild reaction conditions. The generality of the… read more here.
Keywords: annulation; acceptor cyclopropanes; lewis acid; donor acceptor ... See more keywords
Enantioselective [4+2] Annulation to the Concise Synthesis of Chiral Dihydrocarbazoles
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DOI: 10.1016/j.isci.2020.100840
Abstract: Summary A highly efficient phosphine-catalyzed enantioselective [4 + 2] annulation of allenoates with 3-nitroindoles or 3-nitrobenzothiophenes has been developed. The protocol represents a unique dearomatization–aromatization process to access functionalized dihydrocarbazoles or dihydrodibenzothiophenes with high optical… read more here.
Keywords: annulation; concise synthesis; synthesis chiral; enantioselective annulation ... See more keywords
Two Catalytic Annulation Modes via Cu-Allenylidenes with Sulfur Ylides that Are Dominated by the Presence or Absence of Trifluoromethyl Substituents
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DOI: 10.1016/j.isci.2020.100994
Abstract: Summary We disclose the Cu-catalyzed enantioselective synthesis of 3-methyl-3-propargyl-indolines, which contain a quaternary stereogenic carbon center, via the decarboxylative [4 + 1] annulation of 4-methyl-4-propargyl-benzoxazinanones with variety of sulfur ylides. The reaction proceeds predominantly through… read more here.
Keywords: annulation; allenylidene intermediates; sulfur ylides; attack allenylidene ... See more keywords
Cerium(IV) based oxidative free radical cyclization of active methylene compounds with some cyclic alkenes: A useful annulation method for terpene functionalization
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DOI: 10.1016/j.tet.2019.03.039
Abstract: Abstract Ceric ammonium nitrate-mediated oxidative cyclizations of CH-acids with terpenes and terpene like substrates were investigated. Dimedone, acetylacetone, and methyl nitroacetate were condensed with pinene, norbornene, nopol, camphene, and carvone and the reaction stereoselectivity was… read more here.
Keywords: free radical; radical cyclization; annulation; cerium based ... See more keywords
Rhodium(III)-Catalyzed Oxidative Annulation of 4-Aminoquinolines and Acrylate through Two Consecutive C(sp2)-H Activations.
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DOI: 10.1021/acs.orglett.0c00630
Abstract: The C-H annulation of the five-position of quinolines and acrylates to afford heterocycles is an active field of research in organic synthesis. Herein the annulation of 4-aminoquinolines with acrylates through two consecutive C-H activations catalyzed… read more here.
Keywords: two consecutive; annulation; iii catalyzed; annulation aminoquinolines ... See more keywords
Palladium-Catalyzed [5 + 2] Annulation of Vinylethylene Carbonates with Barbiturate-Derived Alkenes.
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DOI: 10.1021/acs.orglett.0c02508
Abstract: A palladium/XantPhos-catalyzed [5 + 2] annulation of VECs with electron-deficient alkenes having an isolated carbon-carbon double bond has been developed to afford spirobarbiturate-tetrahydrooxepines. This study provides an expedient assembly of biologically interesting spirobarbiturate-tetrahydrooxepines. The easy… read more here.
Keywords: annulation; vinylethylene carbonates; carbonates barbiturate; palladium catalyzed ... See more keywords
In(OTf)3-Catalyzed Synthesis of 2,3-Dihydro-1H-benzo[e]indoles and 2,3-Dihydrobenzofurans via [3 + 2] Annulation.
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DOI: 10.1021/acs.orglett.0c02729
Abstract: An In(OTf)3-catalyzed intermolecular [3 + 2] annulation for the synthesis of 2,3-dihydro-1H-benzo[e]indoles and 2,3-dihydrobenzofurans from readily available substrates has been achieved. This approach takes advantage of oxetane and para-quinone methide as important functional units in… read more here.
Keywords: indoles dihydrobenzofurans; otf catalyzed; annulation; benzo indoles ... See more keywords
NHC-Catalyzed Enantioselective [3 + 3] Annulation to Construct 5,6-Dihydropyrimidin-4-ones.
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DOI: 10.1021/acs.orglett.0c02832
Abstract: The unprecedented enantioselective NHC-catalyzed [3 + 3] annulation of α-bromoenals with amidines via a dual C-N bond formation is described. The protocol allows a rapid preparation of 5,6-dihydropyrimidinones in acceptable yields with good enantioselectivities. read more here.
Keywords: annulation; construct dihydropyrimidin; nhc catalyzed; catalyzed enantioselective ... See more keywords
Metal-Free-Catalyzed Three-Component [2+2+2] Annulation Reaction of [60]Fullerene, Ketones, and Indoles: Access to Diverse [60]Fullerene-Fused 1,2-Tetrahydrocarbazoles.
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DOI: 10.1021/acs.orglett.1c00195
Abstract: The first example of metal-free-catalyzed multicomponent annulation reaction of [60]fullerene has been developed for concise and efficient construction of novel [60]fullerene-fused 1,2-tetrahydrocarbazoles. Using inexpensive and readily available I2 as a catalyst, [60]fullerene, ketones, and indoles… read more here.
Keywords: annulation; free catalyzed; fullerene; metal free ... See more keywords
Zinc-Enabled Annulation of Trifluorodiazoethane with 2H-Azirines to Construct Trifluoromethyl Pyrazolines, Pyrazoles, and Pyridazines.
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DOI: 10.1021/acs.orglett.1c02139
Abstract: A diethylzinc-promoted unconventional annulation reaction of 2,2,2-trifluorodiazoethane with 2H-azirines is described. This transformation involves two [3 + 2] cycloaddition steps and one dinitrogen extrusion process in one pot, thus giving a broad array of 3-trifluoromethyl… read more here.
Keywords: annulation; trifluoromethyl pyrazolines; trifluoromethyl; zinc enabled ... See more keywords