Publications by Qian Wang | EPFL Graph Search

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Copper-catalyzed coupling of ortho-aminophenylboronic acid pinacol esters with β-ketoesters afforded, under mild base-free oxidative conditions, 2,3-disubstituted indoles featuring a key Chan-Lam type carbon-carbon bond forming reaction. ...

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 ...

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 ...

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 ...

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 ...

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 ...

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 ...

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 ...

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 ...

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 ...

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 ...

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 ...

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 ...

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 ...

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 ...

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 ...

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 ...

We report herein an enantioselective total synthesis of (-)-artatrovirenol A, a structurally unprecedented cage-like sesquiterpenoid. The synthesis features the following key steps: (a) cationic chiral oxazaborolidinium-catalyzed Diels-Alder reaction betwe ...

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 ...

Qian Wang

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Synthesis of Indoles by Copper-Catalyzed Heteroannulation of o-Aminophenylboronic Acid Pinacol Esters with β-Keto Esters

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

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

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

Organocatalytic Enantioselective Vinylogous Pinacol Rearrangement Enabled by Chiral Ion Pairing

A Concise Total Synthesis of (±)-Trigonoliimine B

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

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

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

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

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

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

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

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

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

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

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

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

Enantioselective Total Synthesis of (-)-Artatrovirenol A

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