Publications associées à Leaving group

(4+3) Annulation of Donor-Acceptor Cyclopropanes and Azadienes: Highly Stereoselective Synthesis of Azepanones

Azepanes are important seven-membered heterocycles, which are present in numerous natural and synthetic compounds. However, the development of convergent synthetic methods to access them remains challenging. Herein, we report the Lewis acid catalyzed (4+3) ...

Wiley-VCH Verlag GmbH2022

Access to Vinyl Ethers and Ketones with Hypervalent Iodine Reagents as Oxy-Allyl Cation Synthetic Equivalents

Jérôme Waser, Nina Declas

We report an Umpolung strategy of enol ethers to generate oxy-allyl cation equivalents based on the use of hypervalent iodine reagents. Under mild basic conditions, the addition of nucleophiles to aryloxy-substituted vinylbenziodoxolone (VBX) reagents, eas ...

Wiley-VCH Verlag GmbH2020

Towards the Sarpagine-Ajmaline-Macroline Family of Indole Alkaloids: Enantioselective Synthesis of an N-Demethyl Alstolactone Diastereomer

Qian Wang, Jieping Zhu, Dylan Jean Robert Dagoneau

the strategy involving the use of functionalized tetrahydro-6H-cycloocta[b]indol-6-one is reported as a key intermediate for synthesis of members of the sarpagine-ajmaline-macroline family of monoterpene indole alkaloids. The desired tricycle was synthesiz ...

WILEY-V C H VERLAG GMBH2020

Neutral chiral cyclopentadienyl Ru(II)Cl catalysts enable enantioselective [2+2]-cycloadditions

Nicolai Cramer, David Kossler

Cyclopentadienyl ruthenium(II) complexes with a large number of available coordination sites are frequently used catalysts for a broad range of transformations. To be able to render these transformations enantioselective, we have designed a chiral neutral ...

2017

Polyimidazolium Salts: Robust Catalysts for the Cycloaddition of Carbon Dioxide into Carbonates in Solvent-Free Conditions

Paul Joseph Dyson, Zhaofu Fei, Felix Daniel Bobbink, Wei Zhong

There is a growing interest in sustainable heterogeneous catalysts based on organic polymers. Here, we describe a series of polyimidazolium salt catalysts, prepared from the direct reaction of arene- bridged bis- and tris-alkyl halides with trimethylsilyli ...

Wiley-V C H Verlag Gmbh2017

"Palladium-Catalyzed Diamination of Alkynes in Synthesis of Tetracycles" and "Copper-Catalyzed Cyanoalkylation of Unactivated Alkenes"

Minh Tu Ha

The thesis deals with the development of transition metal-catalyzed difunctionalization of alkenes and alkynes, which can be categorized into two major topics: (1) palladium-catalyzed diamination of alkynes for the synthesis of tetracycles; (2) copper-cata ...

EPFL2017

Equilibria and Speciation of Chloramines, Bromamines, and Bromochloramines in Water

Jeremy Samuel Arey, Daniela Trogolo

The stabilities and speciation of the halamines in water are difficult to characterize experimentally. We provide theoretical estimates of aqueous standard free energies of formation for inorganic chloramines, bromamines, and bromochloramines, based on hig ...

Amer Chemical Soc2017

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

Qian Wang, Jieping Zhu, Thomas Bertrand Pascal Marie Buyck, Delphine Pasche

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 ...

Wiley-Blackwell2016

Benziodoxol(on)e Reagents as Tools in Organic Synthesis: The Background behind the Discovery at the Laboratory of Catalysis and Organic Synthesis

Jérôme Waser

In this review, a personal account of our work in the field of hypervalent iodine reagents is presented. Pioneering experiments, which led to the discovery of the exceptional reactivity of EthynynnnlBenziodoXol( on)e (EBX) reagents as electrophilic alkyne ...

2016

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

Qian Wang, Jieping Zhu, 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