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Jieping Zhu

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Publications associées (194)

Ketenimines from Isocyanides and Allyl Carbonates: Palladium-Catalyzed Synthesis of β,γ-Unsaturated Amides and Tetrazoles

Qian Wang, Jieping Zhu, Mathias Mamboury, Guanyinsheng Qiu

The reaction of allyl ethyl carbonates with isocyanides in the presence of a catalytic amount of Pd(OAc)2 provided ketenimines through b-hydride elimination of the allyl imidoylpalladium intermediates. The insertion of the isocyanide into the p-allyl Pd co ...

Wiley-Blackwell2016

Enantioselective Total Synthesis of (−)-Terengganensine A

Cyril Piemontesi, Qian Wang, Jieping Zhu

A seven-step enantioselective total synthesis of (-)-terengganensine A, a complex heptacyclic monoterpene indole alkaloid, was accomplished. Key steps included: a) Noyori's catalytic enantioselective transfer hydrogenation of the iminium salt to set up the ...

Wiley-Blackwell2016

Copper-Catalyzed Formal [2+2+1] Heteroannulation of Alkenes, Alkylnitriles, and Water: Method Development and Application to a Total Synthesis of (±)-Sacidumlignan D

Qian Wang, Jieping Zhu, Minh Tu Ha, Claire Chatalova Sazepin

A copper-catalyzed three-component reaction of alkenes, alkylnitriles, and water affords gamma-butyrolactones in good yields. The domino process involves an unprecedented hydroxy-cyanoalkylation of alkenes and subsequent lactonization with the creation of ...

Wiley-Blackwell2016

Chiral Phosphoric Acid Catalyzed Asymmetric Ugi Reaction by Dynamic Kinetic Resolution of the Primary Multicomponent Adduct

Jieping Zhu

Reaction of isonitriles with 3-(arylamino)isobenzofuran-1(3H)-ones in the presence of a catalytic amount of an octahydro (R)-binol-derived chiral phosphoric acid afforded 3-oxo-2-arylisoindoline-1-carboxamides in high yields with good to high enantioselect ...

Wiley-Blackwell2016

Catalytic Asymmetric Tandem Reaction of Tertiary Enamides: Expeditious Synthesis of Pyrrolo[2,1-a]isoquinoline Alkaloid Derivatives

Jieping Zhu

Reported is a new and efficient strategy for rapid construction of the chiral tetrahydropyrrolo[2,1-a]isoquinolin-3(2H)-one structure from unique tertiary enamide synthons. A Cu(OTf)2/chiral Pybox complex catalyzes the intramolecular enantioselective addit ...

Wiley-Blackwell2016

Switchable [3+2] and [4+2] Heteroannulation of Primary Propargylamines with Isonitriles to Imidazoles and 1,6-Dihydropyrimidines: Catalyst Loading Enabled Reaction Divergence

Qian Wang, Jieping Zhu, Shuo Tong

Isonitrile 1 due to its carbene-like reactivity serves generally as a one-carbon synthon in a diverse set of organic transformations. We report in this article that the isocyano group can also act as a polarized triple bond to undergo, as a two-atom syntho ...

Wiley-Blackwell2016

Palladium-Catalyzed Enantioselective Domino Heck/Intermolecular C–H Bond Functionalization: Development and Application to the Synthesis of (+)-Esermethole

Qian Wang, Jieping Zhu, Wangqing Kong

Intramolecular asymmetric carbopalladation of N-aryl acrylamides followed by intermolecular trapping of the resulting σ-C(sp3)−Pd complex by azoles afforded 3,3-disubstituted oxindoles in good yields with excellent enantioselectivities. Two C−C bonds were ...

American Chemical Society2015

2-(Methoxycarbonyl)ethyl as a Removable N-Protecting Group: Synthesis of Indoloisoquinolinones by Pd(II)-Catalyzed Intramolecular Diamination of Alkynes

Qian Wang, Bo Yao, Jieping Zhu, Minh Tu Ha

Pd(II)-catalyzed double cyclization of 1,2-diarylethynes bearing an N-methyl-N-[2-(methoxycarbonyl)ethyl]amino and an aminocarbonyl group at the ortho positions of the two aromatic rings afforded the tetracyclic N-[2-(methoxycarbonyl)-ethyl]indoloisoquinol ...

Amer Chemical Soc2015

Enantioselective Synthesis of Putative Lipiarmycin Aglycon Related to Fidaxomicin/Tiacumicin B

Jieping Zhu

An enantioselective synthesis of a putative lipiarmycin aglycon was accomplished and features: 1) Brown’s enantioselective alkoxyallylboration and allylation of aldehydes, 2) chain elongation by iterative Horner–Wadsworth– Emmons olefination, 3) Evans aldo ...

Wiley-Blackwell2015

Sulfonamide and Tertiary Amine as Nucleophiles in Pd(II)-Catalyzed Diamination of Alkynes: Synthesis of Tetracyclic Indolobenzothiazine S,S‑Dioxides

Qian Wang, Bo Yao, Jieping Zhu, Minh Tu Ha

Pd(II)-catalyzed oxidative double cyclization of the 1,2-diarylethynes bearing an N-methyl-N-(2-methoxycarbonyl)ethylamino and an aminosulfonyl group afforded indolobenzothiazine S,S-dioxides in good to excellent yields. The 2-(methoxycarbonyl)ethyl group ...

American Chemical Society2015

Total Syntheses of (−)-Mersicarpine, (−)-Scholarisine G, (+)-Melodinine E, (−)-Leuconoxine, (−)-Leuconolam, (−)-Leuconodine A, (+)-Leuconodine F, and (−)-Leuconodine C: Self-Induced Diastereomeric Anisochronism (SIDA) Phenomenon for Scholarisine G and Leuconodines A and C

Qian Wang, Jieping Zhu, Zhengren Xu

Enantioselective total syntheses of title natural products from a common cyclohexenone derivative (S)-18 were reported. Ozonolysis of (S)-18 afforded a stable diketo ester (R)-17 that was subsequently converted to two skeletally different natural products, ...

Amer Chemical Soc2015

Synthesis of diverse di- to penta-substituted 1,2-dihydropyridine derivatives from gold(I)-catalyzed intramolecular addition of tertiary enamides to alkynes

Jieping Zhu

As 3-aza-1,5-enynes, internal and terminal alkyne-bearing tertiary enamides underwent an efficient Au(I)-catalyzed 6-endo-dig cyclization reaction to afford a variety of di- to penta-substituted 1,2-dihydropyridine derivatives in high yields. The cyclizati ...

Elsevier2015

Tuning the Reactivity of Isocyano Group: Synthesis of Imidazoles and Imidazoliums from Propargylamines and Isonitriles in the Presence of Multiple Catalysts

Qian Wang, Jieping Zhu, Shuo Tong

The reaction of propargyl amines with tert-butylisonitrile in the presence of a catalytic amount of both Yb(OTf)3 and AgOTf afforded imidazoles, whereas the same reaction with primary and secondary alkylisonitriles, as well as arylisonitriles, in the prese ...

Wiley-Blackwell2015

Integrated One-Pot Synthesis of 1,3-Oxazinan-2-ones from Isocyanoacetates and Phenyl Vinyl Selenones

Qian Wang, Thomas Bertrand Pascal Marie Buyck, Jieping Zhu

Brønsted base (Et3N or DBU) catalyzed Michael addition of α-substituted α-isocyanoacetates to phenyl vinyl selenones followed by a Brønsted acid (PTSA) catalyzed domino oxidative cyclization afforded 1,3-oxazinan-2-ones in good to excellent yields. Enantio ...

Schweizerische Chemische Gesellschaft2015

Chiral Calcium–BINOL Phosphate Catalyzed Diastereo- and Enantioselective Synthesis of syn-1,2-Disubstituted 1,2-Diamines: Scope and Mechanistic Studies

Jieping Zhu

A highly enantioselective, chiral, Lewis acid calcium–bis(phosphate) complex, Ca[3a]n, which catalyzes the electrophilic amination of enamides with azodicarboxylate derivatives 2 to provide versatile chiral 1,2-hydrazinoimines 4 is disclosed. The reaction ...

Wiley-Blackwell2015

Copper-Catalyzed Intermolecular Carboetherification of Unactivated Alkenes by Alkyl Nitriles and Alcohols

Qian Wang, Jieping Zhu, Claire Chatalova Sazepin

A three-component carboetherification of unactivated alkenes has been developed allowing the rapid building of complexity from simple starting materials. A wide range of a-substituted styrenes underwent smooth reactions with unactivated alkyl nitriles and ...

Wiley-Blackwell2015

Pd-Catalyzed Dehydrogenative Aryl−Aryl Bond Formation via Double C(sp2)−H Bond Activation: Efficient Synthesis of [3,4]-Fused Oxindoles

Qian Wang, Ala Bunescu, Jieping Zhu

A Pd(0)-catalyzed double cyclization of easily available o-bromoanilides leading to strained [3,4]-fused oxindoles was developed. The reaction proceeded through a highly ordered sequence involving key carbopalladation, 1,4-Pd migration, and C(sp2)−H functi ...

2015

An Enantioselective Total Synthesis of (−)-Isoschizogamine

Qian Wang, Jieping Zhu, Zhengren Xu, Xu Bao

A concise enantioselective total synthesis of (¢)- isoschizogamine, a complex bridged polycyclic monoterpene indole alkaloid, was accomplished. N-Alkylation of an enantio- enriched imine with an alkyl iodide afforded an iminium salt, which, upon heating by ...

Wiley-Blackwell2015

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

Qian Wang, Jieping Zhu, Zhengren Xu, Mathias Mamboury, Shuo Tong

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 ...

Wiley-Blackwell2015

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

Qian Wang, Ala Bunescu, Jieping Zhu

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 ...

Wiley-Blackwell2015

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