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Chemoselective, Substrate‐directed Fluorination of Functionalized Cyclopentane β‐Amino Acids
Author(s) -
Kiss Loránd,
n Melinda,
Sillanpää Reijo,
Haukka Matti,
Fustero Santos,
Fülöp Ferenc
Publication year - 2016
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201601046
Subject(s) - cyclopentane , norbornene , chemistry , amino acid , substrate (aquarium) , halogenation , ring (chemistry) , organic chemistry , double bond , carbon fibers , stereochemistry , materials science , polymerization , polymer , biochemistry , oceanography , geology , composite number , composite material
This work describes a substrate‐directed fluorination of some highly functionalized cyclopentane derivatives. The cyclic products incorporating CH 2 F or CHF 2 moieties in their structure have been synthesized from diexo ‐ or diendo ‐norbornene β‐amino acids following a stereocontrolled strategy. The synthetic study was based on an oxidative transformation of the ring carbon–carbon double bond of the norbornene β‐amino acids, followed by transformation of the resulted „ all cis “ and „ trans “ diformyl intermediates by fluorination with „chemodifferentiation“.