Abstract
The halogen-catalyzed (I 2, Br 2, and Cl 2) Mukaiyama aldol (MA) reactions were investigated by ab initio MO calculations. The halogen-catalyzed MA reaction between a trihydrosilyl enol ether and formaldehyde favors a concerted pathway. In sharp contrast, the I 2-catalyzed reaction between 1-phenyl-1-(trimethylsilyloxy)ethylene and benzaldehyde favors a stepwise mechanism. The nature of the substituent strongly influences the type of mechanism involved.
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