An Insight into Substrate‐Dependent Fluorination of some Highly Substituted Alicyclic Scaffolds. Issue 10 (7th April 2017)

• Record Type: Journal Article
• Authors: Kiss, Loránd; Petrovszki, Ágnes; Vass, Csaba; Nonn, Melinda; Sillanpää, Reijo; Haukka, Matti; Fustero, Santos; Fülöp, Ferenc
• Is Part Of: ChemistrySelect. Volume 2:Issue 10(2017)
• Page Start: 3049
• Page End: 3052
• Publication Date: 2017-04-07
• Subjects: amino acids -- cyclization -- fluorine -- heterocycles -- lactones; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201700403
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: The substrate‐dependent fluorination of some highly‐functionalized cyclopentane derivatives with multiple chiral centers has been investigated. The key steps of the stereocontrolled syntheses are the oxidative cleavage of the ring carbon–carbon double bond of readily available diexo or diendo norbornene β‐amino acid derivatives followed by transformation of the resulted dialdehyde stereoisomers by reduction. Finally, substrate‐directable chemodifferentiation of different types of hydroxy groups under fluorination procedures gave various densely functionalized alicyclic derivatives or heterocycles. Abstract : The substrate‐directed fluorination of some highly‐functionalized cyclopentane derivatives with multiple chiral centers has been investigated. The key steps of the stereocontrolled syntheses are the oxidative ring cleavage of the ring olefin bond of readily available diexo or diendo norbornene β‐amino acid derivatives followed by transformation of the resulted dialdehyde stereoisomers by fluorination with chemodifferentiation.