Computational study on the Rh-catalyzed chemodivergent oxidative annulation of benzamides and enynes

Abstract

The mechanisms of Cp*Rh(OAc)2-catalyzed coupling reaction of N-methoxybenzamide with alkyl-terminated enyne have been investigated by density functional theory (DFT) calculations. With the addition of NaOAc and changing solvent, the product transforms from lactam P1 in reaction A to iminolactone P2 in reaction B, due to the formed stable OAc-coordinated intermediate. The electronic effect and steric effect account for the observed regioselectivity in reaction B collectively.