Catalyst-Controlled Divergent Intramolecular Cyclizations of Morita-Baylis-Hillman Carbonates

Unprecedented catalyst-controlled divergent cyclizations of Morita-Baylis-Hillman carbonates have been established using either Cs2CO3 or quinuclidine as the catalyst. 1,2-Dihydroquinolines and 4H-3,1-benzoxazines were efficiently synthesized via S(N)2' and S(N)2'-S(N)2' processes, respectively. DFT calculations have led to a deeper understanding of these reaction modes and chemoselectivity.

Automated summary

The unprecedented catalyst-controlled divergent cyclizations of Morita-Baylis-Hillman carbonates have been established, leading to efficient synthesis of 1,2-dihydroquinolines and 4H-3,1-benzoxazines. DFT calculations have provided a deeper understanding of these reaction modes and chemoselectivity.