Previous work from our group has shown that highly substituted ?-lactams can be synthesized through a formal cycloaddition reaction using imines and a-thiosuccinic anhydrides. We have developed a new analogous reaction by replacing the thio substituent with a nitrile. The scope of this reaction is explored, including the use of chiral amines as auxiliaries. Computational studies on the mechanism and origin of the diastereoselectivity of this reaction will be discussed.

Diastereoselective Mannich-type reactions of α-cyano succinic anhydrides with imines leading to complex γ-lactams

245th National Meeting (2013)

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