The aldol reaction is a powerful carbon�carbon bond forming reaction in organic chemistry. Recently a phosphonic acid has been shown to be an effective catalyst for some substrates that are traditionally low-yielding in the aldol reaction.  Our research seeks to further extend the usefulness of this type of catalysis to include unactivated aldehydes through the use of imine derivatives of enolizable aldehydes and ketones. We have found that a phosphonic acid successfully promotes an aldol-type reaction between a citronellal-derived imine and benzaldehyde with moderate yield.  We will report the significant features of the chemistry in response to variations in the reaction conditions as well as our investigation into the scope of the reaction.

Phosphonic acid promoted aldol-type reactions between imines and unactivated aldehydes

243rd National Meeting (2012)

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