Abstract
[3+(2+1)] Annulation represents the most straightforward and atom‐economical strategies in organic synthesis for the efficient construction of diverse cyclic structural units and complex molecules. Herein, we present a Lewis acid Sc(OTf)3‐catalyzed controlled synthesis of two different regioselective oxa/thio‐spirohydroquinolines (C=C at the α/β‐site of O/S‐atom) from aromatic amines and bimolecular O/S‐heterocyclic ketones via intermolecular [3+(2+1)] annulation. This method features mild reaction conditions, high step economy and atom utilization, and the O/S‐heterocyclic ketone can act as both two‐ and one‐carbon synthons. Furthermore, density functional theory (DFT) calculations indicate that the intrinsic cause of this unique regioselectivity is caused by the proton abstraction step.
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.