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Qian Wang

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Related publications (225)

Triple Role of Phenylselenonyl Group Enabled a One-Pot Synthesis of 1,3-Oxazinan-2-ones From α-Isocyanoacetates, Phenyl Vinyl Selenones, and Water

Qian Wang, Thomas Bertrand Pascal Marie Buyck, Jieping Zhu

Reaction of α-substituted α-isocyanoacetates with phenyl vinyl selenones in the presence of a catalytic amount of base (DBU or Et3N, 0.05− 0.1 equiv) followed by addition of p-toluenesulfonic acid (PTSA, 0.1−0.2 equiv) afforded 4,4,5-trisubstituted 1,3-oxa ...

Amer Chemical Soc2014

Total Synthesis of (±)-Aspidophylline A

Qian Wang, Jieping Zhu, Weiwu Ren

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- ...

Wiley-Blackwell2014

Copper-Mediated/Catalyzed Oxyalkylation of Alkenes with Alkylnitriles

Qian Wang, Ala Bunescu, Jieping Zhu

A copper-promoted oxyalkylation of alkenes with alkylnitriles has been developed. The protocol provides rapid access to phthalides (g-lactones) or isochromanones (d-lactones) via the formation of a C(sp3)C(sp3) and a C(sp3)O bond with the generation of up ...

Wiley-Blackwell2014

Copper-catalyzed three-component synthesis of 5-acetamidoimidazoles from carbodiimides, acyl chlorides and isocyanides

Qian Wang, Jieping Zhu, Giulia Sapuppo

2014

Three-Component Povarov Reaction–Heteroannulation with Arynes: Synthesis of 5,6-Dihydroindolo[1,2‑a]quinolines

Qian Wang, Ala Bunescu, Jieping Zhu

A reaction of 2-acyl substituted tetrahydroquinolines, prepared by Lewis acid-catalyzed three-component reaction of α-oxo aldehydes, anilines, and dienophiles, with in situ generated arynes afforded 5,6-dihydroindolo[1,2-a]- quinolines in good to excellent ...

Amer Chemical Soc2014

From Racemic to Enantioselective Total Synthesis of Trigonoliimines via Development of an Organocatalytic Enantioselective Michael Addition of α-Aryl-α-isocyanoacetate to Vinyl Phenyl Selenone

Qian Wang, Thomas Bertrand Pascal Marie Buyck, Jieping Zhu

Trigonoliimines are hexacyclic bisindole alkaloids isolated recently by Hao and co-workers. A synthesis of (±)-trigonoliimine B was accomplished in seven steps from simple starting materials featuring the Bischler-Napieralski reaction for closing the seven ...

Schweizerische Chemische Gesellschaft2014

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

Olivier Wagnières, Qian Wang, Jieping Zhu, Zhengren Xu

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 ...

Amer Chemical Soc2014

Phosphoric Acid Catalyzed Desymmetrization of Bicyclic Bislactones Bearing an All-Carbon Stereogenic Center: Total Syntheses of (−)-Rhazinilam and (−)-Leucomidine B

Jean-Baptiste Gualtierotti, Qian Wang, Jieping Zhu, Delphine Pasche

In the presence of a catalytic amount of an imidodiphosphoric acid, enantioselective desymmetrization of bicyclic bislactones by reaction with alcohols took place smoothly to afford enantiomerically enriched mono acids having an all-carbon stereogenic cent ...

Wiley-Blackwell2014

Mechanistic Study on the Palladium(II)-Catalyzed Synthesis of 2,3-Disubstituted Indoles Under Aerobic Conditions: Anion Effects and the Development of a Low-Catalyst-Loading Process

Qian Wang, Bo Yao, Jieping Zhu

As a result of detailed mechanistic and kinetic studies, we have proposed that PdX2-catalyzed oxidative coupling of o-alkynylanilines 1 with terminal alkynes 2 under aerobic conditions is initiated by aminopalladation of 1 followed by ligand exchange of th ...

Wiley-Blackwell2014

Tertiary Amines as Synthetic Equivalents of Vinyl Cations: Zinc Bromide Promoted Coupling of Propargylamines with α-Isocyanoacetamides To Give 2,4,5-Trisubstituted Oxazoles Initiated by an Internal Redox Process

Qian Wang, Jieping Zhu

Crabe interrupted: Propargylamines 1 react with a-isocyanoacetamides 2 in the presence of zinc bromide to afford vinyl oxazoles 3. The transformation, wherein the propargylamine acts as a vinyl cation synthetic equivalent, involves a domino sequence incorp ...

Wiley-Blackwell2013

Enantioselective Total Syntheses of Leuconolam–Leuconoxine–Mersicarpine Group Monoterpene Indole Alkaloids

Qian Wang, Jieping Zhu, Zhengren Xu

A unified strategy allowing enantioselective total syntheses of (−)-mersicarpine, (−)-scholarisine G, (+)-melodinine E, (−)-leuconoxine, and (−)-leuconolam from a common cyclohexenone derivative was reported. The Suzuki−Miyaura reaction was used to couple ...

2013

Palladium-Catalyzed Through-Space C(sp3)-H and C(sp2)-H Bond Activation by 1,4-Palladium Migration: Efficient Synthesis of [3,4]- Fused Oxindoles

Qian Wang, Ala Bunescu, Jieping Zhu

Palladium two step: Linear anilides were converted into the title compounds in good to excellent yields through a palladium-catalyzed domino carbopalladation/1,4-palladium shift sequence. The C(sp3)-H activation involves a seven-membered palladacycle, and ...

Wiley-Blackwell2013

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

Qian Wang, Bo Yao, Jieping Zhu

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 ...

Wiley-Blackwell2013

Synthesis of Iminonitriles by Oxone/TBAB-Mediated One-Pot Oxidative Three-Component Strecker Reaction

Jean-Baptiste Gualtierotti, Xavier Schumacher, Qian Wang, Jieping Zhu

Oxidative three-component reaction of aldehydes, amines, and TMSCN in a biphasic solvent system (toluene/H2O) containing Oxone, tetra-n-butylammonium bromide (TBAB) and sodium bicarbonate afforded α-iminonitriles in good to excellent yields. This oxidative ...

Georg Thieme Verlag2013

Heteroannulation of arynes with N-aryl-α-aminoketones for the synthesis of unsymmetrical N-aryl-2,3-disubstituted indoles: an aryne twist of Bischler–Möhlau indole synthesis

Cyril Piemontesi, Qian Wang, Ala Bunescu, Jieping Zhu

Reaction of 2-(trimethylsilyl)aryl triflates 1 with N-aryl-a-amino ketones 2 afforded N-aryl-2,3-disubstituted indoles in good to excellent yields with complete control of the substitution patterns. This methodology allowed for the first time a one-step sy ...

Royal Society of Chemistry2013

Zinc Bromide Promoted Coupling of Isonitriles with Carboxylic Acids To Form 2,4,5-Trisubstituted Oxazoles

Qian Wang, Jieping Zhu, Shuo Tong

Deviant behavior: In a deviation from “normal” reactivity, isocyanides underwent co-trimerization with carboxylic acids in the presence of ZnBr2 to smoothly provide oxazoles (see scheme). The reaction is thought to occur by initial nucleophilic addition of ...

Wiley-Blackwell2013

Palladium-Catalyzed Decarboxylative Vinylation of Potassium Nitrophenyl Acetate: Application to the Total Synthesis of (±)-Goniomitine

Qian Wang, Jieping Zhu, Zhengren Xu

Merge and divert. (±)-goniomitine was synthesized featuring two key steps: a) fragment coupling to functionalized cyclopentene by a novel palladium-catalyzed decarboxylative vinylation reaction and b) an unprecedented one-pot integrated oxidation/reduction ...

Wiley-Blackwell2013

Catalytic Enantioselective Michael Addition of α-Aryl-α-Isocyanoacetates to Vinyl Selenone: Synthesis of α,α-Disubstituted α-Amino Acids and (+)- and (−)-Trigonoliimine A

Qian Wang, Thomas Bertrand Pascal Marie Buyck, Jieping Zhu

Be like Mike: The title reaction in the presence of the catalyst 1 afforded Michael adducts in excellent yields and enantioselectivities. The adducts were readily converted into alpha,alpha’-disubstituted alpha-amino acids. The enantioselective total synth ...

Wiley-Blackwell2013

Amidation of Aldehydes and Alcohols through α-Iminonitriles and a Sequential Oxidative Three-Component Strecker Reaction/Thio-Michael Addition/Alumina-Promoted Hydrolysis Process to Access β-Mercaptoamides from Aldehydes, Amines, and Thiols

Jean-Baptiste Gualtierotti, Xavier Schumacher, Qian Wang, Jieping Zhu

Mild and general alumina promoted hydrolysis conditions for converting α-iminonitriles into carboxamides have been developed. In combination with the oxidative three-component Strecker reaction, the one-pot direct amidation of aldehydes and alcohols is rep ...

Wiley-Blackwell2012

A Concise Total Synthesis of (±)-Trigonoliimine B

Qian Wang, Thomas Bertrand Pascal Marie Buyck, Jieping Zhu

Trigonoliimine B, a hexacyclic alkaloid, is synthesized in seven steps from simple starting materials. The synthesis features the use of an alpha-isocyanoacetate as a glycine template for the preparation of an alpha,alpha-disubstituted alpha-amino ester th ...

2012

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