A DFT Study on the NHC-Catalyzed Reaction of Enals with Aminoacrylates: Mechanism, Regioselectivity, and Stereoselectivity
Yan Li,
Junjie Xiao,
Yanlong Kang
et al.
Abstract:DFT (M06-2X) calculations were used to study the NHC-catalyzed [3 + 3] cycloaddition of enals with aminoacrylates. The catalytic cycle begins with the binding of the NHC to enal. Subsequent intramolecular proton transfer generates the Breslow intermediate. This intermediate undergoes an oxidative reaction, leading to the formation of an acyl azolium intermediate, which further reacts with the other substrate aminoacrylate via a new C− C bond formation. This step determines the stereoselectivity of the current … Show more
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