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Jieping Zhu

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Publications associées (194)

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

Qian Wang, Jieping Zhu, Mathias Mamboury

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 ...

Wiley-Blackwell2017

Silver Nitrate-Catalyzed Isocyanide Insertion/Lactamization Sequence to Imidazolones and Quinazolin-4-ones: Development and Application in Natural Product Synthesis

Qian Wang, Jieping Zhu, Antonin François Roland Clemenceau

Silver nitrate-catalyzed reaction of methyl α,α-disubstituted α-isocyanoacetates with primary amines afforded 3,5,5-trisubstituted imidazolones in good to excellent yields. A silver salt-catalyzed insertion of the isocyano group into the N−H bond of the am ...

American Chemical Society2017

Catalytic Enantioselective Double Carbopalladation/C−H Functionalization with Statistical Amplification of Product Enantiopurity: A Convertible Linker Approach

Qian Wang, Jieping Zhu, Shuo Tong, Aurore Kamilia Limouni

Combining a catalytic enantioselective reaction with dimerization in a single operation is an efficient way to upgrade the enantiomeric excesses (ee) of the product. Palladium-catalyzed reaction of N-(2-iodophenyl)-N-methyl methacrylamide derivatives with ...

Wiley-Blackwell2017

Water as a Hydride Source in Palladium-Catalyzed Enantioselective Reductive Heck Reactions

Qian Wang, Jieping Zhu, Wangqing Kong

Pd-catalyzed intramolecular asymmetric carbopalladation of N-aryl acrylamides followed by reduction of C(sp3)-Pd intermediate using diboron–water as a hydride source afforded enantioenriched 3,3-disubstituted oxindoles in high yields and enantioselectiviti ...

Wiley-Blackwell2017

Fluorophores for Excited-State Intramolecular Proton Transfer by an Yttrium Triflate Catalyzed Reaction of Isocyanides with Thiocarboxylic Acids

Qing He, Qian Wang, Jieping Zhu, Shun Zhao, Shuo Tong

Discovery of new chemical reactivity of a given functional group can often result in innovative synthesis of important chemical entities that possess unprecedented properties. We designed and developed a one-step synthesis of 5-amino-4-carboxamidothiazoles ...

Wiley-Blackwell2017

Copper-Catalyzed Three-Component Carboazidation of Alkenes with Acetonitrile and Sodium Azide

Qian Wang, Ala Bunescu, Jieping Zhu, Minh Tu Ha

A copper-catalyzed three-component reaction of alkenes, acetonitrile, and sodium azide afforded gamma-azido alkyl nitriles by formation of one C(sp3)-C(sp3) bond and one C(sp3)-N bond. The transformation allows concomitant introduction of two highly versat ...

Wiley-Blackwell2017

To each his own: isonitriles for all flavors. Functionalized isocyanides as valuable tools in organic synthesis

Jieping Zhu, Andrea Basso

The term functionalized isocyanides refers to all those isocyanides in which a neighbouring functional group can finely tune the reactivity of the isocyano group or can be exploited in post-functionalization processes. In this manuscript, we have reviewed ...

Royal Society of Chemistry2017

Silver-Catalyzed Three-Component 1,1-Aminoacylation of Homopropargylamines: α-Additions for Both Terminal Alkynes and Isocyanides

Cyril Piemontesi, Qian Wang, Jieping Zhu, Shuo Tong

The reaction of secondary homopropargylamines, isocyanides, and water in the presence of a catalytic amount of silver acetate and subsequent purification by chromatography on silica gel afforded substituted proline amides in good to excellent yields. Prima ...

Wiley-Blackwell2017

Organocatalytic Enantioselective Acyloin Rearrangement of α-Hydroxy Acetals to α-Alkoxy Ketones

Qian Wang, Jieping Zhu, Hua Wu

We report an unprecedented organocatalytic enantioselective acyloin rearrangement of alpha,alpha-disubstituted alpha-hydroxy acetals. In the presence of a catalytic amount of chiral binol-derived N-triflyl phosphoramide, alpha-hydroxy acetals rearranged to ...

Wiley-Blackwell2017

Copper-Catalyzed Enantioselective Domino Arylation/Semipinacol Rearrangement of Allylic Alcohols with Diaryliodonium Salts

Qian Wang, Jieping Zhu, Hua Wu

A copper-catalyzed enantioselective arylative semipinacol rearrangement of allylic alcohols was developed. In the presence of a catalytic amount of an in situ generated chiral copper-bisoxazoline complex, reaction of allylic alcohols with diaryliodonium sa ...

Wiley-Blackwell2017

Palladium-Catalyzed Enantioselective Narasaka-Heck Reaction/Direct C−H Alkylation of Arenes: Iminoarylation of Alkenes

Qian Wang, Jieping Zhu, Xu Bao

A palladium-catalyzed reaction of g,d-unsaturated oxime esters with oxadiazoles afforded dihydropyrroles in good to excellent yields through an intramolecular iminopalladation/intermolecular direct heteroarene C-H alkylation cascade. This unprecedented imi ...

Wiley-Blackwell2017

Copper-catalysed cyanoalkylative cycloetherification of alkenes to 1,3-dihydroisobenzofurans: development and application to the synthesis of citalopram

Qian Wang, Jieping Zhu, Minh Tu Ha

A copper-catalysed cyanoalkylative cycloetherification of alkenes was developed. Heating a solution of substituted (2-vinylphenyl)methanol in MeCN/MeOH (v/v 7/3) in the presence of a catalytic amount of copper(II) tetrafluoroborate hydrate [Cu(BF4)26H2O], ...

Royal Society of Chemistry2016

Synthesis of Vinyl Isocyanides and Development of a Convertible Isonitrile

Qian Wang, Jieping Zhu, Martina Spallarossa

The reaction of isocyanomethylenetriphenylphosphorane, generated in situ from the corresponding phosphonium salt, with a diverse set of aldehydes afforded vinyl isocyanides in good to high yields. Excellent E-selectivity was observed for aliphatic aldehyde ...

American Chemical Society2016

Enantioselective Total Syntheses of (−)-Rhazinilam, (−)-Leucomidine B, and (+)-Leuconodine F

Qian Wang, Jieping Zhu, Zhengren Xu, Dylan Jean Robert Dagoneau

A divergent total synthesis of three structurally distinct natural products from imine 9 was accomplished through an approach featuring: 1) a Pd-catalyzed decarboxylative cross-coupling, and 2) heteroannulation of 9 with bromoacetaldehyde and oxalyl chlori ...

Wiley-Blackwell2016

Organocatalytic Enantioselective Vinylogous Pinacol Rearrangement Enabled by Chiral Ion Pairing

Qian Wang, Jieping Zhu, Hua Wu

An enantioselective pinacol rearrangement of functionalized (E)-2-butene-1,4-diols was developed. In the presence of a catalytic amount of a chiral BINOL-derived N-triflyl phosphoramide, these 1,4-diols rearranged to b,g-unsaturated ketones in excellent yi ...

Wiley-Blackwell2016

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

Qian Wang, Jieping Zhu, Yang Wang

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 ...

Wiley-Blackwell2016

Total Synthesis of (±)-Strictamine

Qian Wang, Jieping Zhu, Weiwu Ren

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 ...

Wiley-Blackwell2016

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

Qian Wang, Jieping Zhu, Wangqing Kong

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 ...

Wiley-Blackwell2016

Enantioselective Synthesis of Quaternary α-Amino Acids Enabled by the Versatility of the Phenylselenonyl Group

Qian Wang, Jieping Zhu, Antonin François Roland Clemenceau

A novel Cinchona alkaloid-catalyzed enantioselective conjugate addition of alpha-alkyl substituted alpha-nitroacetates to phenyl vinyl selenone was developed. The resulting enantio-enriched alpha,alpha-dialkyl substituted alpha-nitroacetates were subsequen ...

Wiley-Blackwell2016

Synthesis of Oxazolidin-2-ones by Oxidative Coupling of Isonitriles, Phenyl Vinyl Selenone, and Water

Qian Wang, Thomas Bertrand Pascal Marie Buyck, Jieping Zhu, Delphine Pasche

Reaction of alkyl isocyanides, phenyl vinyl selenone, and water in the presence of a catalytic amount of Cs2CO3 afforded oxazolidin-2-ones in good yields. This unprecedented heteroannulation process created four chemical bonds in a single operation with th ...

Wiley-Blackwell2016

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