ol7b03859_si_001.pdf (11.37 MB)
Spatiotemporal Control of Pre-existing Alkene Geometry: A Bio-Inspired Route to 4‑Trifluoromethyl‑2H‑chromenes
journal contribution
posted on 2018-01-16, 18:50 authored by Svenja
I. Faßbender, Jan B. Metternich, Ryan GilmourRoutes to prepare C4-trifluoromethyl
analogues of the 2H-chromene scaffold are scarce:
this is particularly striking
given the importance of fluorine in pharmaceutical development. To
address this limitation, a facile strategy has been developed that
is reliant on catalytic, geometric isomerization of easily accessible
allylic alcohols (up to >95:5) followed by intramolecular cyclization
via Pd catalysis (up to 96%). This concise biomimetic approach emulates
the photoisomerization/cyclization cascade inherent to phenylpropanoid
biosynthesis.
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Bio-Inspired RoutestrategyC 4-trifluoromethyl analoguesfluorineSpatiotemporal ControlTrifluoromethylphenylpropanoid biosynthesisbiomimetic approach emulateslimitationPre-existing Alkene Geometryphotoisomerizationintramolecular cyclizationimportance2 HPd catalysischromene scaffoldcascadeallylic alcoholsisomerization
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