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    Au(i)-catalyzed intramolecular oxidative cyclopropanation of 1,6-enynes derived from propiolamides with diphenyl sulfoxide
    Organic & Biomolecular Chemistry (2013)
    Hyun-Suk YeomSeunghoon Shin
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    Abstract:
    We have developed gold(I)-catalyzed oxidative cyclopropanation of 1,6-enynes derived from propiolamides employing diphenyl sulfoxide as an oxidant. 1,6-Enynes having a terminal alkyne and a propiolamide tether efficiently transformed into cyclopropane carboxaldehyde derivatives.
    Keywords:
    Cyclopropane
    Sulfoxide
    Alkyne
    Topics:
    Cyclopropane Reaction Mechanisms
    Catalytic Alkyne Reactions
    Catalytic C–H Functionalization Methods
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    Cyclopropane
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    Chemical Science (2023)
    Yulong WangShenyu ShenChonglong HeYoukang ZhouKeyuan Zhang
    A highly atom- and step-economy and diastereoselective copper-mediated direct intramolecular cyclopropanation method to synthesize cyclopropane-fused γ-lactones and lactams from distal olefinic acetate was disclosed.
    Cyclopropane
    Citations (10)
    Au(i)-catalyzed intramolecular oxidative cyclopropanation of 1,6-enynes derived from propiolamides with diphenyl sulfoxide
    Organic & Biomolecular Chemistry (2013)
    Hyun-Suk YeomSeunghoon Shin
    We have developed gold(I)-catalyzed oxidative cyclopropanation of 1,6-enynes derived from propiolamides employing diphenyl sulfoxide as an oxidant. 1,6-Enynes having a terminal alkyne and a propiolamide tether efficiently transformed into cyclopropane carboxaldehyde derivatives.
    Cyclopropane
    Sulfoxide
    Alkyne
    Citations (39)
    Asymmetric synthesis of orthogonally protected trans-cyclopropane γ-amino acids via intramolecular ring closure
    Organic & Biomolecular Chemistry (2006)
    David J. FoxDaniel Sejer PedersenStuart Warren
    The synthesis of enantiomerically-enriched trans-cyclopropane amino- and hydroxy-acids can be achieved by intramolecular ring closure in moderate to good yields. The optically active cyclopropane precursors are easily prepared in a short sequence from inexpensive, commercially available olefins and tert-butyl acetate. Several leaving groups and bases were compared for the cyclopropanation step, showing that the diphenylphosphinate and tosyl leaving groups give the best results when used in combination with either LDA or NaHMDS.
    Cyclopropane
    Closure (psychology)
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    ChemInform Abstract: Ru(II)—Pheox‐Catalyzed Asymmetric Intramolecular Cyclopropanation of Electron‐Deficient Olefins.
    ChemInform (2015)
    Yoko NakagawaSoda ChanthamathKazutaka ShibatomiSeiji Iwasa
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    Natural product
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    ChemInform Abstract: Stereoselective Synthesis of Donor-Acceptor Cyclopropapyranone by Intramolecular Cyclopropanation of Vinylogous Carbonates: Application to the Total Synthesis of (.+-.)-Diospongin B.
    ChemInform (2016)
    Santosh J. GharpureSumit P. ManeLaxmi Narayan NandaManoj K. Shukla
    Abstract The stereo‐ and regioselective cyclopropanation of vinylogous carbonates utilizes CuI/Cu powder as a catalyst to get access to donor—acceptor substituted cyclopropapyranones.
    Acceptor
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    PIII-Mediated intramolecular cyclopropanation and metal-free synthesis of cyclopropane-fused heterocycles
    Chemical Communications (2020)
    Jiayong ZhangJiahang HaoZhiqiang HuangJie HanZhengjie He
    The carbene-like reactivity of the Kukhtin–Ramirez adduct enables the first reductive intramolecular cyclopropanation, which provides easy access to highly functionalized cyclopropane-fused heterocycles.
    Cyclopropane
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    Novel Intramolecular Cyclopropanation Reaction of Unsaturated β‐Keto Esters.
    ChemInform (2003)
    Dan YangQiang GaoChi‐Sing LeeKung‐Kai Cheung
    Abstract For Abstract see ChemInform Abstract in Full Text.
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    Metal-free intramolecular cyclopropanation of alkenes through iodonium ylide methodology
    Tetrahedron (2010)
    Robert M. MoriartySachin TyagiMark A. Kinch
    Cyclopropane
    Ylide
    Reductive elimination
    Intramolecular reaction
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    Ru(II)–Pheox-Catalyzed Asymmetric Intramolecular Cyclopropanation of Electron-Deficient Olefins
    Organic Letters (2015)
    Yoko NakagawaSoda ChanthamathKazutaka ShibatomiSeiji Iwasa
    The first highly enantioselective intramolecular cyclopropanation of electron-deficient olefins, in the presence of Ru(II)--Pheox catalyst, is reported. The corresponding cyclopropane-fused γ-lactones were obtained in high yields (up to 99%) with excellent enantioselectivities (ee up to 99%). Moreover, this method enables efficient access to enantioenriched dicarbonyl cyclopropane derivatives, which are important intermediates for the synthesis of various bioactive compounds.
    Cyclopropane
    Citations (39)