We have developed a diastereoselective, transition metal-catalyzed version of the aza-Cope rearrangement—Mannich cyclization using readily accessible imines as substrates. These substrates obviate the need for a protecting group, resulting in 2,4-<i>cis</i> acyl pyrrolidines in good to excellent stereoselectivities. Reactions proceed under mild conditions using substoichiometric amounts of transition metal, but require an additive for optimum yield. Studies directed toward elucidating the role of the additive and the scope of the reaction will be reported. 

Aza-Cope rearrangement—Mannich cyclizations of imines: A protecting-group free route to acyl pyrrolidines

250th National Meeting (2015)

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