Publication | Open Access
Direct and Stereoselective Alkylation of Nitro Derivatives with Activated Alcohols in Trifluoroethanol
26
Citations
42
References
2012
Year
EngineeringOrganic ChemistryChemistryChemical EngineeringNovel OrganocatalystsActivated AlcoholsDerivativesDiversity-oriented SynthesisFluorous SynthesisCatalysisAsymmetric CatalysisEnantioselective SynthesisNitro DerivativesStereoselective AlkylationNatural SciencesPropargylic AlcoholsDerivative (Chemistry)Synthetic ChemistryChiral Pyrrolidine OrganocatalystPractical Alkylation
Abstract Herein we disclose the simple, effective, and practical alkylation of nitroalkanes that takes place with benzylic, benzhydrylic, and propargylic alcohols in trifluoroethanol. A variety of different nitroalkanes bearing functional groups can be used in this S N 1‐type reaction to afford the desired products in quantitative yields. Different chiral nitro derivatives were submitted to this highly diastereoselective alkylation reaction with selected benzhydrols. A new, effective, and chiral pyrrolidine organocatalyst was prepared by using this methodology.
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