Divergent Asymmetric Total Synthesis of (−)‐Voacafricines A and B

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Dearomatization of electron poor six-membered N-heterocycles through [3+2] annulation with aminocyclopropanes

Jérôme Waser, Johannes Preindl, Shyamal Chakrabarty

Many abundant and highly bioactive natural alkaloids contain an indolizidine skeleton. A simple, high yielding method to synthesize this scaffold from N-heterocycles was developed. A wide range of pyridines, quinolines and isoquinolines reacted with donor- ...

2017

Organocatalysis: Fundamentals and Comparisons to Metal and Enzyme Catalysis

Pierre Vogel

Catalysis fulfills the promise that high-yielding chemical transformations will require little energy and produce no toxic waste. This message is carried by the study of the evolution of molecular catalysis of some of the most important reactions in organi ...

2016

Carbon Dioxide Based N-Formylation of Amines Catalyzed by Fluoride and Hydroxide Anions

Paul Joseph Dyson, Felix Daniel Bobbink, Martin Hulla, Shoubhik Das

We described herein a simple approach for N-formylation with CO2 and hydrosilane reducing agents. Fluoride and hydroxide salts efficiently catalyzed the reaction, principally through activation of the hydrosilanes, which led to hydrosilane reactivities com ...

Wiley-VCH Verlag2016

Mild synthesis of mercaptonitriles from vinyl nitriles and their cyclization reactions

Frank Nüesch, Antonia Neels

Thiol-ene addition of thioacetic acid A is widely used in the synthesis of thiols from vinyl precursors, but so far has not been conducted on non-conjugated vinyl nitriles. The challenge when vinyl nitriles are used is to selectively conduct the thiol-ene ...

Royal Soc Chemistry2016

Synthesis of diverse di- to penta-substituted 1,2-dihydropyridine derivatives from gold(I)-catalyzed intramolecular addition of tertiary enamides to alkynes

Jieping Zhu

As 3-aza-1,5-enynes, internal and terminal alkyne-bearing tertiary enamides underwent an efficient Au(I)-catalyzed 6-endo-dig cyclization reaction to afford a variety of di- to penta-substituted 1,2-dihydropyridine derivatives in high yields. The cyclizati ...

Elsevier2015

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

Jieping Zhu, Nicolas George

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 ...

Wiley-Blackwell2014

Aqueous Oxidation of Sulfonamide Antibiotics: Aromatic Nucleophilic Substitution of an Aniline Radical Cation

Jeremy Samuel Arey, Peter Rudolf Tentscher

Sulfonamide antibiotics are an important class of organic micropollutants in the aquatic environment. For several, sulfur dioxide extrusion products have been previously reported upon photochemical or dark oxidation. Using quantum chemical modeling calcula ...

2013

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, Xu Yang

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

Kinetic and Mechanistic Investigations of the Oxidation of Tramadol by Ferrate and Ozone

Urs von Gunten, Saskia Gisela Zimmermann-Steffens

The kinetics and oxidation products (OPs) of tramadol (TRA), an opioid, were investigated for its oxidation with ferrate (Fe(VI)) and ozone (O-3). The kinetics could be explained by the speciation of the tertiary amine moiety of TRA, with apparent second-o ...

2012

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

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