ol6b00757_si_001.pdf (874.99 kB)
Type 1 Ring-Opening Reactions of Cyclopropanated 7‑Azabenzonorbornadienes with Organocuprates
journal contribution
posted on 2016-04-07, 16:06 authored by Emily Carlson, William TamThe first nucleophilic
ring-opening reactions of cyclopropanated
7-azabenzonorbornadienes have been achieved using organocuprates.
Tricyclic or tetracyclic γ-lactams were obtained as the sole
product in good yields of up to 98% when alkoxycarbonyl groups occupied
the N-substituent position. Successful conversions to lactams were
observed for primary, secondary, tertiary, and aromatic nucleophiles,
as well as for a variety of substrates functionalized on the benzene
ring. A possible mechanism for these transformations is discussed.