کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
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1313907 | 1499357 | 2012 | 5 صفحه PDF | دانلود رایگان |
Backbone-homologated amino acids containing the vicinal difluoride motif have been synthesised in a highly stereoselective manner. The key synthetic transformation is the DeoxoFluor®-mediated fluorination of a vicinal fluorohydrin. The synthetic route is amenable to the production of all possible stereoisomers of α,β-difluoro-γ-aminobutyric acid. In addition, a novel difluoromethyl-substituted β-amino acid is accessed via an unexpected rearrangement process.
Backbone homologated amino acids containing vicinal-difluoro and geminal-difluoro motifs have been synthesised in a stereoselective manner.Figure optionsDownload as PowerPoint slideHighlights
► Fluorinated β- and γ-amino acids have been synthesised.
► All possible stereoisomers can be selectively accessed.
► The key transformation is a modest-yielding deoxyfluorination of a vicinal fluorohydrin.
► Several fluorinating reagents were investigated including DeoxoFluor™, PBSF and XtalFluor-E®.
Journal: Journal of Fluorine Chemistry - Volume 143, November 2012, Pages 143–147