Regio- and diastereoselective synthesis of (3,4,8,9)-dibenzo-2,7-dioxa-5,10-diaza[4.4.4] propellanes from 4-substituted 1,2-cyclohexanediones and o-aminophenols, a computational approach to regioselectivity prediction

The regio- and diastereoselective condensation reactions between 4-Me and 4-t-Bu substituted 1,2-cyclohexanediones and substituted o-aminophenols yielding the [4.4.4] propellane derivatives have been studied. The possibility of using semi-empirical PM3 calculations for rationalization and prediction of the regioisomer formation has been studied.