On the Development of Catalytic Carba-6π Electrocyclizations

Hexatriene substrates substituted in the 2-position with carbonyl groups were studied in the context of catalytic 6 pi electrocyclizations. The nature of the carbonyl group and the substitution pattern on the hexatriene have significant effects on the ability of these substrates to succumb to catalysis. A novel 2-formyl hexatriene dimerization was observed. The first example of a catalytic asymmetric carba-6 pi electrocyclization is reported along with the discovery of an unusual kinetic resolution via a catalytic photochemical electrocyclic ring-opening.