Publications by Jieping Zhu | EPFL Graph Search

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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 ...

Mix and go. The quinidine-amide (1)-catalyzed [2+2] cycloaddition between N-sulfonylimines (2) and alkyl 2,3-butadienoate (3) afforded the (R)-azetidines 4 in excellent yields and enantioselectivities. The (S)-enantiomer was obtained when a quinine-amide c ...

We report herein an asymmetric Pictet– Spengler reaction of α-ketoesters. In the presence of a catalytic amount of simple alanine-derived squaramide and p-nitrobenzoic acid, reaction of tryptamines with methyl 2-oxoalkanoates afforded the corresponding 1- ...

We report herein the enantioselective total synthesis of three monoterpene indole alkaloids, namely, (+)-alstilobanine C, (+)-undulifoline, and (-)-alpneumine H. The key features of our synthesis include: a) introduction of chirality via enantioselective d ...

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 ...

The asymmetric Pictet–Spengler reaction (PSR) with aldehydes is well known. However, PSR involving ketones as electrophilic partners is far-less developed. We report herein the first examples of catalytic enantioselective PSR of tryptamines with α-ketoamid ...

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 ...

A general and practical N-iodosuccinimide (NIS)-promoted aza-Friedel–Crafts reaction of various aromatic nucleophiles with N-acylimines generated in situ from a-amidosulfides to give a rapid access to highly functionalized amines is described. The newly de ...

Heating a DMA/pivalic acid (v/v = 4/1) solution of diversely substituted 6-(phenylamino)hex-2-ynoates in the presence of a catalytic amount of Pd(OAc)2 under oxygen atmosphere afforded pyrrolo[1,2-a]indoles in moderate to good yields. A domino sequence inv ...

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 ...

Potassium phosphate-promoted cross-cyclotetramerization of 2,6-dichloro-3-nitropyridine 1 with resorcinol derivatives 2 gave rise to thermodynamically favored 1,3-alternate tetraoxacalix[2]arene[2]pyridines and kinetically controlled 1,2-alternate isomers. ...

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 ...

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 ...

Jieping Zhu

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

Enantioselective Synthesis of 4-Hydroxytetrahydropyridine Derivatives by Intramolecular Addition of Tertiary Enamides to Aldehydes

Cinchona Alkaloid-Amides Catalyzed Enantioselective Formal [2+2] Cycloadditions of Allenoates and Imines: Enantioselective Synthesis of 2,4-Substituted Azetidines

Organocatalytic Enantioselective Pictet–Spengler Reaction of α‐Ketoesters: Development and Application to the Total Synthesis of (+)‐Alstratine A

Enantioselective Total Synthesis of (+)-Alstilobanine C, (+)-Undulifoline, and (-)-Alpneumine H

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

Catalytic Enantioselective Pictet–Spengler Reaction of α‐Ketoamides Catalyzed by a Single H‐Bond Donor Organocatalyst

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

NIS-Assisted Aza-Friedel-Crafts Reaction with α-Carbamoysulfides as Precursors of

Pd(II)-catalyzed intramolecular aminopalladation/direct C–H arylation under aerobic conditions: synthesis of pyrrolo[1,2-a]indoles

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

Asymmetric Synthesis of Inherently Chiral Tetraoxacalix[2]arene[2]pyridines via SNAr-Based Cross-Cyclotetramerization

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

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