On the Development of Catalytic Carba-6π Electrocyclizations

Abstract

Hexatriene substrates substituted in the 2-position with carbonyl groups were studied in the context of catalytic 6p 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-6p electrocyclization is reported along with the discovery of an unusual kinetic resolution via a catalytic photochemical electrocyclic ring-opening.

Key words

electrocyclic reactions - catalysis - dimerization - asymmetric catalysis - kinetic resolution.

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