Recently we have developed a catalytic version of the aza-Cope rearrangement�Mannich cyclization using boron trifluoride as a Lewis acid catalyst.  In the course of exploring the scope and limitations of this reaction, we uncovered unexpected differences in reaction rate upon altering the iminium cation substituent.  In an effort to more systematically probe the factors influencing the rate and diastereoselectivity of this reaction, we have designed a series of oxazolidines having aryl iminium cation substituents of varying electronic demand.  Based on the aza-Cope�Mannich reactions of these substrates, insight into the rate determining step of this tandem reaction sequence will be reported. 

Substituent effects in the aza-Cope rearrangement—Mannich cyclization

243rd National Meeting (2012)

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