10.1021/acs.orglett.9b02032.s001
Albert Artigas
Albert
Artigas
Jordi Vila
Jordi
Vila
Agustí Lledó
Agustí
Lledó
Miquel Solà
Miquel
Solà
Anna Pla-Quintana
Anna
Pla-Quintana
Anna Roglans
Anna
Roglans
A Rh-Catalyzed Cycloisomerization/Diels–Alder
Cascade Reaction of 1,5-Bisallenes for the Synthesis of Polycyclic
Heterocycles
American Chemical Society
2019
polycyclic derivatives
Polycyclic Heterocycles
intramolecular Rh-catalyzed cycloisomerization
alkene
Cycloisomerization
reactive cycloheptadiene
Rh-Catalyzed
cycloaddition
variety
bisallenes 1
polycyclic dihydroazepine
rhodium
Synthesi
DFT calculations
catalysi
Cascade
regioselective
transformation
novel methodology
entry
Bisallene
dihydrooxepine derivatives
2019-07-11 19:47:44
Journal contribution
https://acs.figshare.com/articles/journal_contribution/A_Rh-Catalyzed_Cycloisomerization_Diels_Alder_Cascade_Reaction_of_1_5-Bisallenes_for_the_Synthesis_of_Polycyclic_Heterocycles/8862233
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 <b>1</b> 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.