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Jieping Zhu

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Publications associées (194)

Organocatalytic Double Ugi Reaction with Statistical Amplification of Product Enantiopurity: A Linker Cleavage Approach To Access Highly Enantiopure Ugi Products

Jieping Zhu, Shuo Tong, Qiang Feng

Here we report an organocatalytic double Ugi reaction combining the enantioselective process and ee enhancement in a single operation to afford the chiral Ugi products with very high ee values. Both bisisocyanides and bisanilines tethered by carbonate and ...

2020

Copper-Catalyzed Cyanoalkylative Aziridination of N-Sulfonyl Allylamines

Qian Wang, Jieping Zhu, Minh Tu Ha, Weisi Guo

Reaction of N-arylsulfonyl allylamines with alkyl nitriles in the presence of di-tert-butyl peroxide (DTBP) and a catalytic amount of copper salt afforded homologated aziridines in 43-86% yield. A sequence involving addition of the in situ generated cyanom ...

Wiley2020

Asymmetric Total Synthesis of (-)-Arborisidine and (-)-19-epi-Arborisidine Enabled by a Catalytic Enantioselective Pictet-Spengler Reaction

Qian Wang, Jieping Zhu, Rémi Julien Sylvain Andres

A five-step total synthesis of arborisidine, a caged pentacyclic monoterpene indole alkaloid, has been accomplished in both racemic and enantioselective manners. The synthesis features the following three key steps: (a) a regioselective Pictet-Spengler rea ...

AMER CHEMICAL SOC2020

Functionalization of remote C(sp3)-H bonds enabled by copper-catalyzed coupling of O-acyloximes with terminal alkynes

Qian Wang, Jieping Zhu, Ruben Omar Torres Ochoa, Zhaodong Li

Transition metal catalyzed Sonogashira cross-coupling of terminal alkynes with aryl(vinyl) (pseudo)halides has been successfully extended to alkyl halides for the synthesis of functionalized internal alkynes. The direct alkynylation of remote unfunctionali ...

Nature Research2020

Towards the Sarpagine-Ajmaline-Macroline Family of Indole Alkaloids: Enantioselective Synthesis of an N-Demethyl Alstolactone Diastereomer

Qian Wang, Jieping Zhu, Dylan Jean Robert Dagoneau

the strategy involving the use of functionalized tetrahydro-6H-cycloocta[b]indol-6-one is reported as a key intermediate for synthesis of members of the sarpagine-ajmaline-macroline family of monoterpene indole alkaloids. The desired tricycle was synthesiz ...

WILEY-V C H VERLAG GMBH2020

Catalytic Enantioselective Benzilic Ester Rearrangement

Qian Wang, Jieping Zhu, Hua Wu

We report the first examples of catalytic enantioselective benzilic ester rearrangement reaction. In the presence of a catalytic amount of Cu(OTf)(2) and a chiral box ligand under mild conditions, reaction of 2,3-diketoesters with alcohols afforded structu ...

Wiley-VCH Verlag GmbH2020

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

Qian Wang, Jieping Zhu, Guihua Chen, Jian Cao

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 ...

2020

Construction of the Erythrinane Core Skeleton via Asymmetric Catalytic Cascade Reaction of Tertiary Enamides

Jieping Zhu, Shuo Tong

We report herein an efficient cascade strategy for the rapid construction of a highly enantioenriched erythrinane core skeleton. Under the sequential catalysis of a chiral Cr(III)(salen)Cl and InCl3, cyclohexanone-derived tertiary enamides undergo an intra ...

2020

Synthesis of Benzo[a]carbazoles through Visible Light-Induced Cycloaromatization

Qian Wang, Bo Yao, Jieping Zhu

We report herein a synthesis of 5,6-diarylbenzo[a]carbazoles by a sequence of 6 pi-electrocyclization followed by beta-elimination. The highly functionalized 2,3-disubstituted indoles used for this cycloaromatization process are prepared by Pd-catalyzed cy ...

WILEY-V C H VERLAG GMBH2020

Catalytic Enantioselective Synthesis and Switchable Chiroptical Property of Inherently Chiral Macrocycles

Jieping Zhu, Shuo Tong, Qiang Feng, Xianfu Zhang

We report herein a strategy to construct enantiopure inherently chiral macrocycles, ABCD-type heteracalix[4]-aromatics, through a catalytic enantioselective intramolecular C−N bond forming reaction. A chiral ligand-palladium complex was found to efficientl ...

2020

Recent Advances in Catalytic Enantioselective Rearrangement

Qian Wang, Jieping Zhu, Hua Wu

Among the fundamental chemical transformations in organic synthesis, rearrangement has been recognized as powerful and reliable reactions for the construction of carbon-carbon or carbon-heteroatom bonds. Benefiting from the advance of the novel catalytic s ...

2019

Dual Photoredox/Copper Catalysis for the Remote C(sp3 )−H Functionalization of Alcohols and Alkyl Halides by N -Alkoxypyridinium Salts

Qian Wang, Jieping Zhu, Xu Bao

Under mild dual photoredox/copper catalysis, the reaction of N-alkoxypyridinium salts with readily available silyl reagents (TMSN3, TMSCN, TMSNCS) afforded d-azido, d-cyano, and d-thiocyanato alcohols in high yields. The reaction went through a domino proc ...

Wiley-VCH Verlag GmbH2019

Copper-catalyzed remote C(sp3)–H azidation and oxidative trifluoromethylation of benzohydrazides

Qian Wang, Jieping Zhu, Xu Bao

The Hofmann-Löffler-Freytag (HLF) reaction is a prototypical example of radical-based remote functionalization of unactivated C(sp3)–H bond. While 1,5-hydrogen atom transfer (1,5-HAT) of the amidyl radical is thermodynamically favorable and is well-establi ...

Springer2019

Copper-Catalyzed 1,2-Methoxy Methoxycarbonylation of Alkenes with Methyl Formate

Qian Wang, Jieping Zhu, Balázs Budai, Alexandre Julien Florent Leclair

Reported here is a copper-catalyzed 1,2-methoxy methoxycarbonylation of alkenes by an unprecedented use of methyl formate as a source of both the methoxy and the methoxycarbonyl groups. This reaction transforms styrene and its derivatives into value-added ...

Wiley-VCH Verlag GmbH2019

Stereoselective Total Synthesis of Eburnane-Type Alkaloids Enabled by Conformation-Directed Cyclization and Rearrangement

Cyril Piemontesi, Qian Wang, Jieping Zhu, Guang Li

Controlling the cis C20/C21 relative stereochemistry remains an unsolved issue in the synthesis of eburnane-type indole alkaloids. Provided herein is a simple solution to this problem by developing a unified and diastereoselective synthesis of four represe ...

Wiley-VCH Verlag GmbH2019

Catalytic Atropenantioselective Heteroannulation between Isocyanoacetates and Alkynyl Ketones: Synthesis of Enantioenriched Axially Chiral 3-Arylpyrroles

Qian Wang, Jieping Zhu, Sheng-Cai Zheng

We report herein the first examples of catalytic enantioselective synthesis of axially chiral 3-arylpyrroles. Reaction of a-isocyanoacetates with b-aryl-a,b-alkynic ketones in the presence of silver oxide and a phosphine ligand derived from Cinchona alkalo ...

Wiley-VCH Verlag GmbH2019

Construction of Quaternary Stereocenters by Palladium-Catalyzed Carbopalladation-Initiated Cascade Reactions

Jieping Zhu, Wangqing Kong, Yulin Li

The enantioselective synthesis of molecules containing quaternary stereocenters is a field of intense research interest and development. Among the known organic transformations, carbopalladation-initiated domino transformations constitutes a general method ...

Wiley-VCH Verlag GmbH2019

Catalytic Enantioselective Pinacol and Meinwald Rearrangements for the Construction of Quaternary Stereocenters

Qian Wang, Jieping Zhu, Hua Wu

The development of enantioselective pinacol rearrangement is extremely challenging due to the likelihood involvement of the carbenium intermediate that renders the stereochemical communication between catalyst and substrate difficult to achieve. Herein, we ...

2019

Catalytic Enantioselective α-Ketol Rearrangement

Qian Wang, Jieping Zhu, Hua Wu, Rémi Julien Sylvain Andres

A highly enantioselective a-ketol rearrangement has been developed. In the presence of a chiral Cu-bisoxazoline complex, achiral b-hydroxy-a-dicarbonyls were isomerized to chiral a-hydroxy-b-dicarbonyls and their bicyclic derivatives in excellent yields an ...

Wiley-VCH Verlag GmbH2019

Catalytic Kinetic Resolution by Enantioselective Aromatization: Conversion of Racemic Intermediates of the Barton-Zard Reaction into Enantioenriched 3-Arylpyrroles

Qian Wang, Jieping Zhu, Sheng-Cai Zheng

Racemic 3,4-dihydro-2H-pyrroles, hypothetical intermediates of the Barton–Zard reaction, were synthesized in a highly diastereoselective manner and fully characterized for the first time. Kinetic resolution of the dihydropyrroles with a quinine-derived thi ...

Wiley-VCH Verlag GmbH2019

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