Lewis acid catalyzed Diels-Alder reactions of 1,2-naphthoquinones.
The use of BF(3) x OEt(2) catalysis in Diels-Alder reactions of 3,4-unsubstituted 1,2-naphthoquinones provides direct access to cis-tetrahydrophenanthrene derivatives in good to excellent yields (66-99%) without rapid adduct aromatization commonly associated with corresponding thermal processes.
School of Chemistry, Monash University, VIC 3800, Australia.
Danny M
DM
Gelman
Craig M
CM
Forsyth
Patrick
P
Perlmutter