Synthetic Use of a ?-Alkyl-?-Allyl Iron Complex Obtained by Stereospecific Ring Openig of α-Pinene

Article abstract of DOI:10.1016/0040-4039(91)80763-V

Insertion of iron carbonyl into the four-membered ring of α-pinene produces a versatile iron complex exhibiting an iron-carbon ?-bond.Reaction of this complex with various reagents, i.e. dimethyl butynedioate, produces the bicyclic ketones 2, 7, and 8 with moderate to high regioselectivity and full conservation of the optical purity of the starting terpene. Key Words: Transition Metal Induced Ring Opening; Natural Product Transformation; Reactivity of Iron-Carbon ?-Bonds; CC Bond Formation; Ring Enlargement.