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A Rh-Catalyzed Cycloisomerization/Diels–Alder Cascade Reaction of 1,5-Bisallenes for the Synthesis of Polycyclic Heterocycles
journal contribution
posted on 2019-07-11, 19:47 authored by Albert Artigas, Jordi Vila, Agustí Lledó, Miquel Solà, Anna Pla-Quintana, Anna RoglansA novel
methodology to transform bisallenes into a variety of polycyclic
derivatives employing rhodium(I) catalysis has been developed. This
transformation encompasses an intramolecular Rh-catalyzed cycloisomerization
of bisallenes 1 to deliver a reactive cycloheptadiene,
which concomitantly undergoes a regioselective [4 + 2] cycloaddition
with alkenes. A complete mechanistic study of this transformation
has been undertaken including DFT calculations. Overall, the methodology
presented here constitutes a new and straightforward entry to polycyclic
dihydroazepine and dihydrooxepine derivatives employing catalytic
methods.
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polycyclic derivativesPolycyclic Heterocyclesintramolecular Rh-catalyzed cycloisomerizationalkeneCycloisomerizationreactive cycloheptadieneRh-Catalyzedcycloadditionvarietybisallenes 1polycyclic dihydroazepinerhodiumSynthesiDFT calculationscatalysiCascaderegioselectivetransformationnovel methodologyentryBisallenedihydrooxepine derivatives
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