Pyrrole

Science de la nature
Chimie
Chimie organique
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Catalytic Atropenantioselective Heteroannulation between Isocyanoacetates and Alkynyl Ketones: Synthesis of Enantioenriched Axially Chiral 3-Arylpyrroles

Qian Wang, Sheng-Cai Zheng, Jieping Zhu

We report herein the first examples of catalytic enantioselective synthesis of axially chiral 3-arylpyrroles. Reaction of a-isocyanoacetates with b-aryl-a,b-alkynic ketones in the presence of silver oxide and a phosphine ligand derived from Cinchona alkalo ...

Wiley-VCH Verlag GmbH2019

Catalytic Kinetic Resolution by Enantioselective Aromatization: Conversion of Racemic Intermediates of the Barton-Zard Reaction into Enantioenriched 3-Arylpyrroles

Qian Wang, Jieping Zhu, Sheng-Cai Zheng

Racemic 3,4-dihydro-2H-pyrroles, hypothetical intermediates of the Barton–Zard reaction, were synthesized in a highly diastereoselective manner and fully characterized for the first time. Kinetic resolution of the dihydropyrroles with a quinine-derived thi ...

Wiley-VCH Verlag GmbH2019

Development of New Strategies of Umpolung with Cyclic Hypervalent Iodine Reagents

Paola Caramenti

Organic chemistry is essential for the development of a modern society and technical progress requires the continuous development of synthetic methodologies Novel, efficient, selective and flexible protocols are employed to access complex frameworks from s ...

EPFL2019

Ligand-Controlled Regiodivergent Hydroalkylation of Pyrrolines

Xile Hu, Deyun Qian

Nickel hydride (NiH) catalyzed hydrocarbonation has emerged as an efficient approach to construct new C-C bonds containing at least one C(sp(3)) center. However, the regioselectivity of this reaction is by far dictated by substrates. Described here is a st ...

Wiley-VCH Verlag GmbH2019

The dilemma between acid and base catalysis in the synthesis of benzimidazole from o-phenylenediamine and carbon dioxide

Paul Joseph Dyson, Martin Hulla, Simon Nussbaum, Alexy Robert Bonnin

The tandem synthesis of benzimidazole and other azoles can be achived by the N-formylation of ortho-substituted anilines followed by a cyclization reaction. However, CO2-based N-formylations with hydrosilane reducing agents are base catalyzed whereas the c ...

Royal Society of Chemistry2019

Asymmetric Alkenyl C−H Functionalization by Cp x Rh III forms 2 H ‐Pyrrol‐2‐ones through [4+1]‐Annulation of Acryl Amides and Allenes

Nicolai Cramer, Shouguo Wang, Yang Liu

An efficient CpxRhIII‐catalyzed enantioselective alkenyl C−H functionalization/[4+1] annulation of acryl amides and allenes is reported. The described transformation provides straightforward access to enantioenriched α,β‐unsaturated‐γ‐lactams bearing a qua ...

Wiley-VCH Verlag GmbH2019

Saddle-like, π-conjugated, cyclooctatetrathiophene-based, hole-transporting material for perovskite solar cells

Mohammad Khaja Nazeeruddin, Iwan Zimmermann, Giulia Grancini, Inés Garcia Benito, Javier Urieta Mora

A flexible, saddle-like, π-conjugated skeleton composed of four fused thiophene rings forming a cyclooctatetrathiophene (CoTh) with four triphenylamines (CoTh-TTPA) is presented as a hole-transporting material (HTM) for perovskite solar cells. The new HTM ...

Royal Society of Chemistry2019

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

Protection Group Effects During α,γ-Diol Lignin Stabilization Promote High-Selectivity Monomer Production

Jeremy Luterbacher, Wu Lan, Masoud Talebi Amiri, Christopher Marc Hunston

Protection groups were introduced during biomass pretreatment to stabilize lignin's α,γ-diol group during its extraction and prevent its condensation. Acetaldehyde and propionaldehyde stabilized the α,γ-diol without any aromatic ring alkylation, which sign ...

Wiley-VCH Verlag GmbH2018

Indole Alkaloids, Macrocycles and Heterocycles : Interplay between Methodological Development and Total Synthesis

Cyril Piemontesi

An enantioselective total synthesis of (-)-terengganensine A, a heptacyclic monoterpene indole alkaloid, was performed. A short sequence allowed to obtain the enantio-enriched target in good overall yield. The synthesis featured a key asymmetric transfer h ...

EPFL2018

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