Carboalumination of Seven-Membered-Ring trans-Alkenes

Seven-membered-ring trans-alkenes undergo rapid hydro- and carboalumination reactions in the absence of a catalyst with complete regio- and diastereoselectivity. Control experiments, including deuterium labeling, adding radical inhibitors, and using a radical clock, suggest that these reactions proceed by a concerted mechanism. The products of the reaction possess a new carbon-aluminum bond that can then undergo subsequent transformations, particularly oxidation, providing functionalized products as single stereoisomers.