Publications by Shuo Tong | EPFL Graph Search

Related publications (22)

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

Jieping Zhu, Qian Wang, Shuo Tong, Shun Zhao

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

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

Jieping Zhu, Qian Wang, 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

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

Jieping Zhu, Qian Wang, 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

Thiazole Boron Difluoride Dyes with Large Stokes Shift, Solid State Emission and Room-Temperature Phosphorescence

Jieping Zhu, Wei Wang, Shuo Tong

The small Stokes shift and weak emission in the solid state are two main shortcomings associated with the boron-dipyrromethene (BODIPY) family of dyes. This study presents the design, synthesis and luminescent properties of boron difluoro complexes of 2-ar ...

WILEY-V C H VERLAG GMBH2022

Inherently chiral nor-heteracalixarenes: design and synthesis via enantioselective intramolecular Suzuki-Miyaura reaction

Jieping Zhu, Shuo Tong

There has been a recent upsurge in research aimed at synthesizing inherently chiral molecules devoid of point, axial, planar and helical chiralities. We present herein our design and enantioselective synthesis of a series of inherently chiral macrocycles. ...

Royal Society of Chemistry (RSC)2024

Lewis acid catalyst-steered divergent synthesis of functionalized vicinal amino alcohols and pyrroles from tertiary enamides

Jieping Zhu, Shuo Tong

We report herein two Lewis acid catalyst-steered distinct reaction pathways of N-formylmethyl tertiary enamides. In the presence of a catalytic amount of AlCl3 and 4 angstrom molecular sieves, the stable N-formylmethyl tertiary enamides underwent sequentia ...

ROYAL SOC CHEMISTRY2018

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

Jieping Zhu, Qian Wang, Shuo Tong, Cyril Piemontesi

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

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

Jieping Zhu, Qian Wang, 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

Synthesis of 4-amino-1,2,3,4-tetrahydropyridine derivatives by intramolecular nucleophilic addition of tertiary enamides to in-situ generated imines

Jieping Zhu, Shuo Tong

The reactivity of stable tertiary enamides in nucleophilic addition reaction with various in-situ generated imines was explored. Under very mild conditions, formyl-bearing tertiary enamides reacted with both aromatic and aliphatic amines to form imine inte ...

Elsevier2012

Catalytic Enantioselective Synthesis of Inherently Chiral Macrocycles by Dynamic Kinetic Resolution

Jieping Zhu, Shuo Tong

Kinetically fast racemization of chiral substrates through an achiral intermediate and enantioselective functionalization of one of the enantiomeric substrates forms the basis of the dynamic kinetic resolution (DKR) of centrally chiral molecules. We report ...

2024

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

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

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

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

Jieping Zhu, Shuo Tong, Qiang Feng

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 ...

2020

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

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

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

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

Jieping Zhu, Shuo Tong

Wiley-Blackwell2012

Highly Strained Oxygen‐Doped Chiral Molecular Belts of the Zigzag‐Type with Strong Circularly Polarized Luminescence

Jieping Zhu, Shuo Tong

Herein we report a two-directional cyclization strategy for the synthesis of highly strained depth- expanded oxygen-doped chiral molecular belts of the zigzag-type. From the easily accessible resorcin[4]arenes, an unprecedented cyclization cascade generati ...

Wiley-VCH Verlag GmbH2023

Chiral phosphoric acid-catalyzed enantioselective three-component Mannich reaction of acyclic ketones, aldehydes and anilines

Qian Wang, Jieping Zhu, Shuo Tong

2018

Asymmetric Synthesis of Enantioenriched Zigzag-Type Molecular Belts by Kinetic Resolution and Subsequent Transformations

Jieping Zhu, Shuo Tong

Asymmetric synthesis of enantioenriched zigzag-type molecular belts featuring copper/H8-binaphthol-catalyzed kinetic resolution of a resorcinarene derivative and subsequent transformations was developed. The acquired rigid and C4-symmetric belt exhibited r ...

2023

Catalytic Enantioselective Synthesis and Switchable Chiroptical Property of Inherently Chiral Macrocycles

Jieping Zhu, Shuo Tong, Xianfu Zhang, Qiang Feng

We report herein a strategy to construct enantiopure inherently chiral macrocycles, ABCD-type heteracalix[4]-aromatics, through a catalytic enantioselective intramolecular C−N bond forming reaction. A chiral ligand-palladium complex was found to efficientl ...

2020

Fused N‐Heterocycles with Contiguous Stereogenic Centers Accessed by an Asymmetric Catalytic Cascade Reaction of Tertiary Enamides

Jieping Zhu, Shuo Tong

We report in this article a cascade reaction strategy for the synthesis of complex N-heterocyclic compounds with contiguous and tetrasubstituted stereogenic carbons. Under the sequential catalysis of a chiral binol–Ti complex and BF3, cyclopentanone-derive ...

2020

Synthesis of Hydroxylated 3,4-Dihydropyridine-2-ones from Intramolecular Nucleophilic Addition Reaction of Oxirane-containing Tertiary Enamides

Jieping Zhu, Shuo Tong

Catalyzed by p-toluenesulfonic acid in dry acetonitrile, oxirane-containing tertiary enamides underwent efficient cyclization via intramolecular addition to produce 3-hydroxy-3,4-dihydropyridin-2(1H)-one derivatives in moderate to good yields. ...

Georg Thieme Verlag2011