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An Insight into Substrate‐Dependent Fluorination of some Highly Substituted Alicyclic Scaffolds
Author(s) -
Kiss Loránd,
Petrovszki Ágnes,
Vass Csaba,
n Melinda,
Sillanpää Reijo,
Haukka Matti,
Fustero Santos,
Fülöp Ferenc
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201700403
Subject(s) - alicyclic compound , cyclopentane , oxidative cleavage , chemistry , norbornene , substrate (aquarium) , ring (chemistry) , double bond , organic chemistry , cleavage (geology) , bond cleavage , stereochemistry , materials science , catalysis , polymer , polymerization , oceanography , composite material , fracture (geology) , geology
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.