A Rh-Catalyzed Cycloisomerization/Diels–Alder
Cascade Reaction of 1,5-Bisallenes for the Synthesis of Polycyclic
Heterocycles
Posted on 2019-07-11 - 19:47
A 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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Artigas, Albert; Vila, Jordi; Lledó, Agustí; Solà, Miquel; Pla-Quintana, Anna; Roglans, Anna (2019). A Rh-Catalyzed Cycloisomerization/Diels–Alder
Cascade Reaction of 1,5-Bisallenes for the Synthesis of Polycyclic
Heterocycles. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.9b02032
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AUTHORS (6)
AA
Albert Artigas
JV
Jordi Vila
AL
Agustí Lledó
MS
Miquel Solà
AP
Anna Pla-Quintana
AR
Anna Roglans
KEYWORDS
polycyclic derivativesPolycyclic Heterocyclesintramolecular Rh-catalyzed cycloisomerizationalkeneCycloisomerizationreactive cycloheptadieneRh-Catalyzedcycloadditionvarietybisallenes 1polycyclic dihydroazepinerhodiumSynthesiDFT calculationscatalysiCascaderegioselectivetransformationnovel methodologyentryBisallenedihydrooxepine derivatives