Selectivities in carbometalation of olefins. Experimental and theoretical studies

Abstract

Despite the potential synthetic utility of the reaction, the elements that control the regio- and stereochemistry of the addition of an organometallic reagent to an olefin have not received careful attention. Our recent studies on the selectivities in organometallic addition to cyclopropenone acetals have revealed some principles of regio- and stereocontrol in organometallic additions to olefins. As guided by the computational analysis of the experimental selectivities, it was found that the controlling elements are quite different from those known for organometallic additions to carbonyl compounds.