10.1021/acs.joc.9b02608.s002
Jothi
Lakshmi Nallasivam
Jothi
Lakshmi
Nallasivam
Tushar Kanti Chakraborty
Tushar Kanti
Chakraborty
Titanocene(III)-Mediated 5‑exo-trig Radical Cyclization: En Route to Spirooxindole-Based Tetrahydrofuran and Bicyclic Lactone
American Chemical Society
2019
exhibit
oxirane-ring
Spirooxindole-Based Tetrahydrofuran
cyclization
Cyclization
Ti
isatin core system
array
availability
Bicyclic Lactone
epoxy-acrylate
En Route
Titanocene
presence
tetrahydrofuran-based oxa-spirooxindole systems
ester
scope
lactone
quaternary center
reductive
opening
importance
spectrum
intramolecular 5- exo-trig
reactive prochiral C -3 position
application
oxa-spirooxindole molecules
oxindole-appended
Radical
Herein
disubstituted
isatin-derived
Cp
spirooxindole heterocyclic motifs
hydroxyl
2019-12-11 13:10:07
Dataset
https://acs.figshare.com/articles/dataset/Titanocene_III_-Mediated_5_exo-trig_Radical_Cyclization_En_Route_to_Spirooxindole-Based_Tetrahydrofuran_and_Bicyclic_Lactone/11353406
The isatin core system is of immense importance due to
the highly reactive prochiral C-3 position, which paves an easy way
to construct large arrays of spirooxindole heterocyclic motifs. Herein,
we depict an isatin-derived and 3,3′-disubstituted oxindole-appended
epoxy-acrylate undergoing Cp<sub>2</sub>Ti(III)Cl-mediated reductive
oxirane-ring opening with concomitant intramolecular 5-exo-trig radical
cyclization leading to tetrahydrofuran-based oxa-spirooxindole systems.
The fused spirooxindole structural feature is embedded in many natural
products and tends to exhibit a wide spectrum of biological activities.
The presence of more than one quaternary center and the availability
of multiple functional groups like hydroxyl, ester, or lactone in
the resultant products expand the scope of synthetic applications
of the newly acquired oxa-spirooxindole molecules.