Spatiotemporal Control of Pre-existing Alkene Geometry:
A Bio-Inspired Route to 4‑Trifluoromethyl‑2H‑chromenes
Posted on 2018-01-16 - 18:50
Routes 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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Faßbender, Svenja
I.; Metternich, Jan B.; Gilmour, Ryan (2018). Spatiotemporal Control of Pre-existing Alkene Geometry:
A Bio-Inspired Route to 4‑Trifluoromethyl‑2H‑chromenes. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.7b03859
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AUTHORS (3)
SF
Svenja
I. Faßbender
JM
Jan B. Metternich
RG
Ryan Gilmour
KEYWORDS
Bio-Inspired RoutestrategyC 4-trifluoromethyl analoguesfluorineSpatiotemporal ControlTrifluoromethylphenylpropanoid biosynthesisbiomimetic approach emulateslimitationPre-existing Alkene Geometryphotoisomerizationintramolecular cyclizationimportance2 HPd catalysischromene scaffoldcascadeallylic alcoholsisomerization