Xinyue Hu

Bio: Xinyue Hu is an academic researcher from Sichuan University. The author has contributed to research in topics: Enantioselective synthesis & Catalytic cycle. The author has an hindex of 3, co-authored 6 publications receiving 60 citations.

Catalytic Asymmetric Inverse-Electron-Demand Hetero-Diels–Alder Reaction of Dioxopyrrolidines with Hetero-Substituted Alkenes

Abstract: A highly efficient enantioselective inverse-electron-demand hetero-Diels–Alder reaction of dioxopyrrolidines with heterosubstituted alkenes has been realized by using a N,N′-dioxide/Ni(II) complex as the catalyst. A series of chiral bicyclic dihydropyranes were generated in excellent yields, good dr, and excellent ee values. Besides, a catalytic cycle with a possible transition state was proposed.

Catalytic asymmetric Nakamura reaction by gold(I)/chiral N,N'-dioxide-indium(III) or nickel(II) synergistic catalysis.

Abstract: Intermolecular addition of enols and enolates to unactivated alkynes was proved to be a simple and powerful method for carbon-carbon bond formation. Up to date, a catalytic asymmetric version of alkyne with 1,3-dicarbonyl compound has not been realized. Herein, we achieve the catalytic asymmetric intermolecular addition of 1,3-dicarbonyl compounds to unactivated 1-alkynes attributing to the synergistic activation of chiral N,N'-dioxide-indium(III) or nickel(II) Lewis acid and achiral gold(I) π-acid. A range of β-ketoamides, β-ketoesters and 1,3-diketones transform to the corresponding products with a tetra-substituted chiral center in good yields with good e.r. values. Besides, a possible catalytic cycle and a transition state model are proposed to illustrate the reaction process and the origin of chiral induction based on the experimental investigations.

Catalytic Asymmetric Diels-Alder Reaction/[3,3] Sigmatropic Rearrangement Cascade of 1-Thiocyanatobutadienes.

Abstract: A highly efficient asymmetric Diels-Alder/[3,3] sigmatropic rearrangement reaction of methyleneindolinones with 1-thiocyanatobutadienes has been realized by using a chiral N,N'-dioxide/nickel(II) complex as the catalyst. A range of cyclohexenyl isothiocyanates were synthesized in high yields with excellent diastereo- and enantioselectivities. Based on mechanistic studies, a catalytic cycle with possible transition-state models were proposed to explain the process.

Catalytic Asymmetric Halogenation/Semipinacol Rearrangement of 3-Hydroxyl-3-vinyl Oxindoles: A Stereodivergent Kinetic Resolution Process.

Abstract: A highly enantioselective halogenation/semipinacol rearrangement of isatin-derived allylic alcohols has been developed with a chiral N,N'-dioxide/ScIII complex as catalyst. This strategy involved a pivotal stereodivergent kinetic resolution process and provided a facile and efficient entry to optically active halo-substituted quinolone derivatives and quinoline alkaloids with a quaternary stereocenter simultaneously under mild reaction conditions. Based on the control experiments together with kinetic studies and DFT calculations, a possible catalytic cycle was proposed to illustrate the reaction process and enantiocontrol.

Catalytic Enantioselective Construction of Spiro Quaternary Carbon Stereocenters

Abstract: The catalytic enantioselective assembly of spirocyclic molecules featuring a spiro quaternary carbon stereocenter is currently of great interest because such privileged 3D structures are widely present in natural products that exhibit a broad spectrum of biological and pharmacological activities. This review summarizes the advances based on six major synthetic strategies and showcases the reaction mechanisms in detail. The advantages and limitations of each synthetic strategy are presented, and the remaining synthetic opportunities are outlined.

Recent advances in organocatalytic asymmetric multicomponent cascade reactions for enantioselective synthesis of spirooxindoles

Abstract: Asymmetric catalytic multicomponent cascade reactions have become indispensable tools for enantioselective construction of spirooxindoles. In recent years, a number of successful strategies have been developed for the synthesis of enantioenriched spirooxindoles in high yield with excellent stereo- and regioselectivity. This review summarizes the recent advances on enantioselective construction of spirooxindoles including spiro[N-heterocycle-oxindoles], spiro[cycloalkane-oxindoles] and spiro[O-heterocycle-oxindoles] catalyzed by chiral phosphoric acids, amines, and bifunctional thiourea/squaramides.

Diastereoselective Construction of Indole-Bridged Chroman Spirooxindoles through a TfOH-Catalyzed Michael Addition-Inspired Cascade Reaction

Abstract: The first highly diastereoselective Michael addition/condensation/Friedel–Crafts alkylation cascade reaction of 3-indolyl-substituted oxindoles with ortho-hydroxychalcones was established, which afforded a wide range of polycyclic indole-bridged chroman spirooxindoles with novel and complex scaffolds in moderate to excellent yields.