Publications by Jieping Zhu | EPFL Graph Search

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The first catalytic asymmetric inverse electron demand 1,3-dipolar cycloaddition of azomethine imines with enecarbamates has been developed. Isoquinolinefused pyrazolidines containing two or three contiguous stereogenic centers were obtained in high yields ...

The structure of uleine type alkaloids is characterized by the presence of a bridged tetracyclic hexahydro-1H-1,5-methanoazocino[4,3-b]indole ring system 1. Various strategies have been developed to access this polycyclic structural motif. We report herein ...

Treatment of o-nitrostyrenes with aqueous TiCl3 solution at room temperature afforded indoles via a formal reductive C(sp2)-H amination process. A range of functions such as halides (Cl, Br), carbonyl (ester, carbamate), cyano, hydroxyl and amino groups we ...

Heck shortens the distance. Palladium-catalyzed activation of C(sp3)-H bond by a σ-alkyl Pd(II) complex generated in situ from a remote arylhalide function is developed. The novel domino carbopalladation/C(sp3)-C(sp3) bond forming process allowed a rapid a ...

The generation of heteroatom-centred radicals (X), followed by intramolecular 1,5-hydrogen atom transfer (1,5-HAT) and the functionalisation of the translocated carbon-centred radicals, is the basic mechanism of the classic Hofmann-Loffler-Freytag (HLF) re ...

A copper-catalyzed alkylation of allylic alcohols by alkyl nitriles with concomitant 1,2-aryl migration was developed. Formation of the alkyl nitrile radical was followed by its intermolecular addition to alkenes and the migration of a vicinal aryl group w ...

Selective three-component 1,2-diamination of 1,3-dienes with concurrent introduction of two orthogonally protected amino groups remains unknown despite its significant synthetic potential. We report herein that reaction of conjugated dienes with N-aminopyr ...

The total synthesis of strictamine has been achieved in nine steps from a known enol triflate. Characteristic features of our approach included: a) creation of a C7 all-carbon quaternary stereocenter at an early synthetic stage; b) use of an N,N-dimethyl t ...

A total synthesis of aspidophylline A, a pentacyclic akuammiline-type monoterpene indole alkaloid, is described. The synthesis features: 1) rapid access to a fully functionalized dihydrocarbazole through the desymmetrization of readily available 2-allyl-2- ...

Born to couple: The Pd(OAc)2-catalyzed reaction of o-alkynylanilines (1) with oalkynylbenzamides (2) affords the cyclizative cross-coupling products 3 in good to excellent yields. Three bonds are created in the formation of two heterocycles tethered by a t ...

An asymmetric synthesis of (+)-stephadiamine has been accomplished featuring (a) an enantioselective dearomatizative Michael addition to generate a quaternary stereocenter; (b) a domino sequence involving reductive generation of nitrone from γ-nitro ketone ...

The palladium-catalyzed reaction of a-haloketones with isocyanides afforded -oxo-ketenimines through alpha-hydride elimination of the beta-oxo-imidoyl palladium intermediates. Reaction of these relatively stable alpha-oxo ketenimines with nucleophiles suc ...

Macrocyclization methodologies allowing access to macrocycles having an endo ary ether and an endo ary-aryl bond, especially those based on an intramolecular SNAr reaction and the Suzuki-Miyaura reaction, were summarized. Total synthesis of complestatin, a ...

In the presence of a catalytic amount of Pd(OAc)2 and a stoichiometric amount of tert-butylamine, the reaction of propargyl carbonates, isocyanides, and alcohols afforded polysubstituted aminopyrroles in good yields. Using water as a nucleophile instead of ...

An unprecedent asymmetric catalytic benzilic amide rearrangement for the synthesis of α,α-disubstituted piperazinones is reported. The reaction proceeds via a domino [4+1] imidazolidination/formal 1,2-nitro- gen shift/1,2-aryl or alkyl migration sequence, ...

Total syntheses of (±)-goniomitine, (±)-1,2-dehydroaspidospermidine, (±)-aspidospermidine, (±)-vincadifformine, and (±)-kopsihainanine A were achieved featuring two common key steps: (1) a palladium-catalyzed decarboxylative vinylation that provides quick ...

The Wacker process, which is widely used to convert monosubstituted alkenes into the corresponding methyl ketones, is thought to proceed through a PdII/Pd0 catalytic cycle involving a b-hydride elimination step. This mechanistic scenario is inapplicable to ...

Reported herein is the synthesis of C4-symmetric chiral resorcin[4]arene macrocycles by a catalytic enantioselective multicomponent reaction. Using (S)-piperidine-2-carboxamide-derived N,N′-dioxide as a chiral organocatalyst, the desymmetrization of resorc ...

Palladium-catalyzed intramolecular carbopalladation of N-aryl acrylamides followed by migratory insertion of an isocyanide-coordinated C(sp3)-Pd intermediate afforded an alkylimidoyl-Pd(II) complex, which can be intercepted by a nucleophile, including hete ...

In the presence of a catalytic amount of Pd(TFA)2 and a chiral Pyox ligand under oxygen atmosphere, oxidative Heck reaction between arylboronic acids and 4- substituted or 4,4-disubstituted cyclopent-1-enes afforded the chiral arylated products with concur ...

Jieping Zhu

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Chiral Phosphoric Acid-Catalyzed Enantioselective Formal [3+2] Cycloaddition of Azomethine Imines with Enecarbamates

Enantioselective Total Synthesis of (+)-Nordasycarpidone, (+)-Dasycarpidone, and (+)-Uleine

Aqueous Titanium Trichloride Promoted Reductive Cyclization of o-Nitrostyrenes to Indoles: Development and Application to the Synthesis of Rizatriptan and Aspidospermidine

Activation of a C(sp3)H Bond by a Transient s-Alkylpalladium(II) Complex: Synthesis of Spirooxindoles Through a Palladium-Catalyzed Domino Carbopalladation/C(sp3)C(sp3) Bond-Forming Process

Visible light photoredox-catalysed remote C-H functionalisation enabled by 1,5-hydrogen atom transfer (1,5-HAT)

Copper-Catalyzed Cyanomethylation of Allylic Alcohols with Concomitant 1,2-Aryl Migration: Efficient Synthesis of Functionalized Ketones Containing an α-Quaternary Center

Selective 1,2-Aminoisothiocyanation of 1,3-Dienes Under Visible-Light Photoredox Catalysis

Total Synthesis of (±)-Strictamine

Total Synthesis of (±)-Aspidophylline A

Palladium(II)-Catalyzed Cyclizative Cross-Coupling of ortho-Alkynylanilines with ortho-Alkynylbenzamides under Aerobic Conditions

Enantioselective Total Synthesis of (+)-Stephadiamine

α-Oxo-Ketenimines from Isocyanides and α-Haloketones: Synthesis and Divergent Reactivity

Access to Macrocycles with an endo Aryl ether and an endo Aryl-Aryl Bond, Development and Application

Palladium-Catalyzed Three-Component Reaction of Propargyl Carbonates, Isocyanides, and Alcohols or Water: Switchable Synthesis of Pyrroles and Its Bicyclic Analogues

Asymmetric Construction of α,α‐Disubstituted Piperazinones Enabled by Benzilic Amide Rearrangement

Unified Strategy to Monoterpene Indole Alkaloids: Total Syntheses of (±)-Goniomitine, (±)-1,2-Dehydroaspidospermidine, (±)-Aspidospermidine, (±)-Vincadifformine, and (±)-Kopsihainanine A

Oxidative rearrangement of 1,1-disubstituted alkenes to ketones

C4-Symmetric Inherently Chiral Macrocycles from Organocatalytic Enantioselective Desymmetrization of Resorcin[4]arenes

Synthesis of Diversely Functionalized Oxindoles Enabled by Migratory Insertion of Isocyanide to a Transient σ-Alkylpalladium(II) Complex

Desymmetrization of Prochiral Cyclopentenes Enabled by Enantioselective Palladium-Catalyzed Oxidative Heck Reaction