Iron-Catalyzed Allylation of Ketones

Significance

The allylation of carbonyl compounds is among the most widely used methods of a new C-C bond formation, as it results in synthetically quite useful homoallylic alcohols. The new protocol for this reaction, described here, advantageously applies allylic acetates instead of conventional allylmetal species. An inexpensive and environmentally benign iron catalyst is used for this transformation. Various ketones and allylic acetates can be successfully used in this reaction, affording the expected products in good yields and regioselectivity. The allylic moiety reacts at the most hindered end of the allylic system, but an equilibration to the thermodynamic linear product occurs after longer reaction times.