Highly stereoselective construction of adjacent tetrasubstituted carbon stereogenic centres via an organocatalytic Mukaiyama-aldol reaction of monofluorinated silyl enol ethers to isatins
Organic Chemistry FrontiersPublished 30 May 2014
Yun‐Lin Liu, Fumin Liao, Yanfei Niu, Xiao‐Li Zhao, Jian Zhou
Citations77
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Abstract
We report the first organocatalytic activation of monofluorinated silyl enol ethers 1, by nucleophilic tertiary amine catalysis, to develop asymmetric reactions for the construction of fully substituted chiral carbons featuring a C–F bond. Accordingly, a highly stereoselective Mukaiyama-aldol reaction of isatins to furnish hydroxyoxindoles bearing two adjacent tetrasubstituted carbon stereocenters is developed.
Keywords
ChemistryPharmacology, Toxicology and Pharmaceutics
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The different strategies to access monofluorocyclopropanes are reported and some of their attractive biological applications are highlighted.
Organic & Biomolecular ChemistryElectrophilic fluorination of organosilanes
74 Citations2005Matthew Tredwell, Véronique Gouverneur
The fluorination of organosilanes with the silyl groups directly attached or adjacent to an aryl or alkenyl group has been only very recently examined and recent results revealed that this chemistry allows for the preparation of a variety of novel fluorinated building blocks including enantio-enriched derivatives.
ChemBioChemThe Influence of Fluorinated Molecules (Semiochemicals and Enzyme Substrate Analogues) on the Insect Communication System
73 Citations2004Cristina Pesenti, Fiorenza Viani
F fluorinated molecules have been developed as probes to elucidate the complex chemorecognition processes of insects, and new analogues have been synthesized to investigate the metabolic pathway of a pheromone molecule and many of them are promising disrupting agents.
Organic Chemistry FrontiersCatalytic fluorination of unactivated C(sp<sup>3</sup>)–H bonds
73 Citations2014Jun‐An Ma, Shen Li
Chemical CommunicationsOrganocatalytic asymmetric synthesis of chiral fluorinated quaternary carbon containing β-ketoesters
72 Citations2009Hao Li, Shilei Zhang +3 more
Organocatalytic enantioselective conjugate addition of alpha-fluoroketoesters to nitroolefins efficiently catalyzed by a cinchona alkaloid-derivative affords versatile non-enolizable ketoesters by forming two consecutive fluorinated quaternary and tertiary chiral carbon centers with excellent enantiOSElectivity.
Organic LettersScandium(III)-Catalyzed Enantioselective Allylation of Isatins Using Allylsilanes
72 Citations2012Nadine V. Hanhan, Yng C. Tang +2 more
The scandium(III)-catalyzed enantioselective Hosomi-Sakurai allylation of isatins with various substituted allylic silanes with the effects of additives and varying silyl groups were explored to demonstrate the scope and application.
SynthesisSolution- and Solid-Phase Approaches in Asymmetric Phase-Transfer Catalysis by Cinchona Alkaloid Derivatives
71 Citations2001Baptiste Thierry, Thierry Perrard +3 more
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