Beilstein J. Org. Chem.2023,19, 66–77, doi:10.3762/bjoc.19.6
Research Center, Institute of Materials Science and Nanotechnology, Bilkent University, Ankara 06800, Turkey 10.3762/bjoc.19.6 Abstract We have developed a catalytic aza-Nazarovreaction of N-acyliminium salts generated in situ from the reaction of a variety of cyclic and acyclic imines with α,β
cyclization of 3,4-dihydroisoquinolines with α,β-unsaturated acyl chlorides gives tricyclic lactam products 7 in up to 79% yield with full diastereocontrol (dr = >99:1). The use of acyclic imines in a similar catalytic aza-Nazarovreaction with 20 mol % of AgOTf results in the formation of α-methylene-γ
on the success of the catalytic aza-Nazarovreaction.
Keywords: α-methylene-γ-lactam; aza-Nazarovreaction; β-silicon effect; heterocycles; intramolecular cyclization; Introduction
The rapid construction of aliphatic heterocycles from acyclic building blocks via cyclization or cycloaddition