Iron-Promoted Carbometalation of Bicyclic Alkenes

Significance

The authors describe a diastereoselective arylation of oxa- and azabicyclic alkenes using iron catalysis. Unlike most of the available desymmetrizations of these strained alkenes (see Review below), the method is selective for arylation without ring opening. After carbometalation, the ensuing alkyl iron intermediate could be trapped with a number of electrophiles, such as iodine, allylbromide and acetylchloride, leading to disubstituted products.

Review: M. Lautens, K. Fagnou, S. Hiebert Acc. Chem. Res. 2003, 36, 48-58.