Publications de Jieping Zhu | EPFL Graph Search

Asymmetric Synthesis of Inherently Chiral Tetraoxacalix[2]arene[2]pyridines via SNAr-Based Cross-Cyclotetramerization

Potassium phosphate-promoted cross-cyclotetramerization of 2,6-dichloro-3-nitropyridine 1 with resorcinol derivatives 2 gave rise to thermodynamically favored 1,3-alternate tetraoxacalix[2]arene[2]pyridines and kinetically controlled 1,2-alternate isomers. ...

2025

Chiral Phosphoric Acid-catalyzed Enantioselective Higher-order Cycloadditions: Temperature-dependent Periselectivity

Matthew Wodrich, Jieping Zhu

Higher-order cycloadditions (HOCs) are powerful tools for constructing complex cyclic structures, but their synthetic utility is often limited by poor periselectivity and challenges in achieving high diastereo- and enantioselectivity. Herein, we report a c ...

AMER CHEMICAL SOC2025

Highly diastereoselective and enantioselective cyclopropanation of alkenes catalyzed by a chiral iridium(III) porphyrin complex

Jieping Zhu

Extensive research has been conducted on chiral porphyrin-metal complex (M = Co, Rh, Ru, Fe)-catalyzed asymmetric cyclopropanation of alkenes. However, the corresponding iridium complex has scarcely been exploited for this purpose. We report herein that th ...

2025

Chemoselectivity in Pd-Based Dyotropic Rearrangement: Development and Application in Total Synthesis of Pheromones

Jieping Zhu

In the dyotropic rearrangement of molecules with semiflexible structures, characterized by a freely rotating static C-C bond, the formation of a mixture of products is common due to the coexistence of several energetically comparable conformers. Herein, we ...

2025

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

Jieping Zhu

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 ...

2025

Total Synthesis of Discobahamin A and Putative Structure of Discobahamin B via an Isocyanide-based Macrocyclization Reaction

Jieping Zhu, Baochao Yang

We report in this paper the first total synthesis of discobahamin A, a 24-membered macrocyclopeptide containing an alpha-keto amide functional group. We assign the absolute configuration of 2-hydroxy-3-methylpentanoic acid (Hmp), the side chain capping the ...

WILEY-V C H VERLAG GMBH2025

Pd-Catalyzed Strain-Releasing Dyotropic Rearrangement: Ring-Expanding Amidofluorination of Methylenecyclobutanes

Jieping Zhu, Guoqiang Yang, Baochao Yang

Under the Pd(II)/Pd(IV) catalytic cycle, the cyclization of pent-4-en-1-amine derivatives typically yields either pyrrolidines or piperidines depending on the N-protecting group. We report herein an unprecedented Pd(II)-catalyzed oxidative domino process t ...

2025

Wacker Oxidation of Trisubstituted Alkenes: Pd(II)‐Catalyzed Oxidative Ring Expansion of Exocyclic α,β‐Unsaturated Carbonyl to 2‐Fluoro‐1,3‐Dicarbonyl Compounds

Jieping Zhu

The Wacker oxidation is a powerful synthetic method widely employed for the transformation of monosubstituted alkenes into methyl ketones. Its substrate scope has progressively expanded to include internal disubstituted and, more recently, gem‐disubstitute ...

Wiley2025

Divergent Enantioselective Total Synthesis of (-)-Ajmalicine, (+)-Mayumbine, and (-)-Roxburghine C

Jieping Zhu

We report herein a divergent enantioselective total synthesis of (-)-ajmalicine, (+)-mayumbine, and (-)-roxburghine C. The synthesis employs Franzen's organocatalytic reaction between N-acetoacetyl tryptamine and (E)-5-hydroxypent-2-enal to generate a func ...

AMER CHEMICAL SOC2025

Chalcogen bonding catalysis

Jieping Zhu

Catalysts play a major role in chemical synthesis, and catalysis is considered to be a green and economic process. Catalysis is dominated by covalent interactions between the catalyst and substrate. The design of non-covalent catalysts came into limelight ...

Royal Society of Chemistry2024

Quaternary Carbon Editing Enabled by Sequential Palladium Migration

Qian Wang, Jieping Zhu, Hua Wu, Takuji Fujii

Peripheral functionalization of a quaternary carbon via C(sp 3)−H bond activation has made significant progress in recent years. However, direct editing of a quaternary carbon through Csp 3 −Csp 3 bond cleavage and refunctionalization of nonstrained acycli ...

American Chemical Society (ACS)2024

Editing Tetrasubstituted Carbon: Dual C–O Bond Functionalization of Tertiary Alcohols Enabled by Palladium-Based Dyotropic Rearrangement

Qian Wang, Jieping Zhu, Baochao Yang, Tristan Corentin Pierre Delcaillau

Many elegant asymmetric syntheses of enantioenriched tertiary alcohols have been developed, and both the transition metal-catalyzed and the radical-based peripheral functionalization of tertiary alcohols have attracted intensive research interest in recent ...

2024

Arylative Ring Expansion of 3-Vinylazetidin-3-Ols and 3-Vinyloxetan-3-Ols to Dihydrofurans by Dual Palladium and Acid Catalysis

Qian Wang, Jieping Zhu, Takuji Fujii

In contrast to the well-studied 1-vinylcyclobu- tanols, the reactivity of 3-vinylazetidin-3-ols 1 and 3- vinyloxetan-3-ols 2 under transition metal catalysis remains largely unexplored. We report herein their unique reactivity under dual palladium and acid ...

Wiley-VCH Verlag GmbH2024

Catalytic Enantioselective Synthesis of Inherently Chiral Macrocycles by Dynamic Kinetic Resolution

Jieping Zhu, Shuo Tong

Kinetically fast racemization of chiral substrates through an achiral intermediate and enantioselective functionalization of one of the enantiomeric substrates forms the basis of the dynamic kinetic resolution (DKR) of centrally chiral molecules. We report ...

2024

Chemoselective Pd-Based Dyotropic Rearrangement: Fluorocyclization and Regioselective Wacker Reaction of Homoallylic Amides

Qian Wang, Jieping Zhu, Chenxu Liu

Fluorocyclization of alkenes tethered with a pronucleophile is an efficient transformation that converts easily accessible starting materials to fluorinated heterocycles in a single step. We report herein an unprecedented Pd(II)-catalyzed oxidative domino ...

American Chemical Society (ACS)2024

Design and Synthesis of C4‐Symmetric Axially Chiral β‐Aryl Porphyrins and Application for Supporting Ir(III)‐Catalyzed Enantioselective C−H Alkylation

Jieping Zhu

A hitherto unknown class of C4-symmetric Caryl Cβ (C3, C8, C13, C18) axially chiral porphyrins has been synthesized and the application of their iridium (Ir) complexes in catalytic asymmetric C(sp3) H functionalization is documented. Cyclotetramerization o ...

Wiley-VCH Verlag GmbH2024

[4+1] Heteroannulation to Form 1‐Pyrrolines through Alder‐Ene Reaction of in situ Generated Ynimines: Development and Application in Total Synthesis of Borrecapine

Qian Wang, Jieping Zhu, Rémi Hugo Lavernhe

We report in this paper a novel Cu-catalyzed synthesis of polysubstituted 1-pyrrolines. The reaction of β,γ-unsaturated oxime esters 4 with terminal alkynes 5 in the presence of a catalytic amount of Cu(OAc)2 and 2,2’-biquinoline affords the corresponding ...

Wiley2024

Inherently chiral nor-heteracalixarenes: design and synthesis via enantioselective intramolecular Suzuki-Miyaura reaction

Jieping Zhu, Shuo Tong

There has been a recent upsurge in research aimed at synthesizing inherently chiral molecules devoid of point, axial, planar and helical chiralities. We present herein our design and enantioselective synthesis of a series of inherently chiral macrocycles. ...

Royal Society of Chemistry (RSC)2024

Benzylic C(sp3)-H Azidation: Copper vs Iron Catalysis

Jérôme Waser, Qian Wang, Jieping Zhu, Raphaël Michel Henri Simonet-Davin, Pierre Gérard Joseph Palamini

The generation of benzylic radicals through hydrogen atom abstraction (HAT) has been a recent research focus and various C(sp(3))-H bond functionalization protocols have been developed relying on this elementary step. We report herein copper- and iron-cata ...

2024

Palladium‐Based Dyotropic Rearrangement Enables A Triple Functionalization of Gem‐Disubstituted Alkenes: An Unusual Fluorolactonization Reaction

Qian Wang, Jieping Zhu, Qiang Feng, Chenxu Liu

We report in this paper a Pd(II)-catalyzed migratory gem-fluorolactonization of ene-carboxylic acids. Reaction of 4-methylenealkanoic acid derivatives with Selectfluor in the presence of Pd(OAc)2 (1.0 mol %) at room temperature affords fluorolactones in go ...

Wiley-VCH Verlag GmbH2024