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 6pi; 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-6pi; electrocyclization is reported along with the discovery of an unusual kinetic resolution via a catalytic photochemical electrocyclic ring-opening.