Concept

Enol

Related publications (30)

Synthesis of (Carbo) nucleoside Analogues by [3+2] Annulation of Aminocyclopropanes

Jérôme Waser, Florian Patrick Marie Daniel De la Barre De Nanteuil, Sophie Lucie Racine, Eloísa Sofía Serrano Robledo

(Carbo) nucleoside derivatives constitute an important class of pharmaceuticals, yet there are only few convergent methods to access new analogues. Here, we report the first synthesis of thymine-, uracil-, and 5-fluorouracil-substituted diester donor-accep ...

Wiley-Blackwell2014

Taming Hypervalent Bonds and Strained Rings for Catalysis and Synthesis

Jérôme Waser, Florian Patrick Marie Daniel De la Barre De Nanteuil, Reto Frei, Yifan Li, Maria Victoria Vita, Sophie Lucie Racine, Eloísa Sofía Serrano Robledo

Improving the synthesis of complex organic molecules is essential for progress in many fields such as medicine, agrochemicals or materials. Since 2007, our laboratory has been focusing on the development of non-classical bond disconnections based on the us ...

2014

Rhodium(III)/Copper(II)-Promoted trans-Selective Heteroaryl Acyloxylation of Alkynes: Stereodefined Access to trans-Enol Esters

Nicolai Cramer, Van Manh Pham

Enol esters are versatile synthetic building blocks which can be elaborated by a wide variety of transformations. The classical synthesis by O-selective enolate acylation often hampers control of the E/Z selectivity with highly substituted substrates. A rh ...

Wiley-Blackwell2014

Diester-Substituted Aminocyclopropanes: Synthesis and Use in [3+2]-Annulation Reactions

Jérôme Waser, Florian Patrick Marie Daniel De la Barre De Nanteuil, Eloísa Sofía Serrano Robledo

In this Letter, we describe the synthesis of new donor-acceptor substituted cyclopropanes bearing various imido groups and their use in [3+2]-annulation reactions. A sequence of palladium-catalyzed vinylation and rhodium-catalyzed cyclopropanation gave acc ...

Georg Thieme Verlag2014

Azidation of beta-Keto Esters and Silyl Enol Ethers with a Benziodoxole Reagent

Jérôme Waser, Maria Victoria Vita

The efficient azidation of beta-keto esters and silyl enol ethers using a benziodoxole-derived azide transfer reagent is reported. The azidation of cyclic beta-keto esters could be achieved in up to quantitative yields in the absence of any catalyst. In th ...

American Chemical Society2013

Ethynylbenziodoxolones (EBX) as Reagents for the Ethynylation of Stabilized Enolates

Jérôme Waser, Jonathan Brand, Davinia Fernández González

Herein, we report a detailed study on the electrophilic alkynylation of cyclic keto esters and amides with ethynylbenziodoxolone (EBX) reagents. The structure and stability of this class of reagents is first described more in details. Differential scanning ...

Wiley-Blackwell2013

Catalytic [3+2] Annulation of Aminocyclopropanes for the Enantiospecific Synthesis of Cyclopentylamines

Jérôme Waser, Florian Patrick Marie Daniel De la Barre De Nanteuil

With nitrogen too: The first catalytic [3+2] annulation of aminocyclopropanes with enol ethers is reported (see scheme; Phth=phthaloyl). The reaction worked with easily accessible phthalimidocyclopropanes using 5 mol % of SnCl4 in nearly quantitative yield ...

Wiley-VCH Verlag GmbH2011

Efficient Asymmetric Synthesis of Long-Chain Polyketides Containing up to Ten Contiguous Stereogenic Centres by Double Chain Elongation

Rosario Scopelliti, Pierre Vogel, Maris Turks

The 2,3-anti-3,4-syn-stereotriad (1Z,2S,3R,4S)-1-ethylidene-2,4-dimethyl-3-[(1S)-1-phenylethoxy]-5-oxopent-1-yl isobutyrate {(-)-8, obtained in a one-pot operation from the trimethylsilyl (Z)-enol ether derived from pentan-3-one and (1E,3Z)-1[(1S)-phenylet ...

2011

Ethynyl-1,2-benziodoxol-3(1 H)-one (EBX): An Exceptional Reagent for the Ethynylation of Keto, Cyano, and Nitro Esters

Jérôme Waser, Jonathan Brand, Davinia Fernández González

Hot alkyne! The in situ generation of Ethynyl-1,2-BenziodoXol-3(1H)-one (EBX) from the corresponding silyl protected reagent using TBAF is reported. EBX displayed exceptional acetylene transfer ability to stabilized enolates, even at –78 °C. The mild react ...

2010

Poly(ethylene glycol) Adlayers Immobilized to Metal Oxide Substrates Through Catechol Derivatives: Influence of Assembly Conditions on Formation and Stability

Karl Gademann

We have investigated Five different poly(ethylene glycol) (PEG, 5 kDa) catechol derivatives in terms of their spontaneous surface assembly from aqueous solution, adlayer stability, and resistance to nonspecific blood serum adsorption as a function of the t ...

2010