Lewis acid catalyzed Diels-Alder reactions of 1,2-naphthoquinones

Org Lett. 2009 Nov 5;11(21):4958-60. doi: 10.1021/ol9021047.

Abstract

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.