Formal cycloaddition between cyanosuccinic anhydrides and various imines lead to efficient diastereoselective synthesis of ?-lactams. Computational elucidation of the mechanism and the origins of stereocontrol in this entire series of reactions are reported. DFT computations revealed that the transformation proceeds through a stepwise Mannich-acylation. The computed free energy barriers and selectivity are in agreement with experiments. The diastereocontrol arises from a combination of hydrogen bonding & CH���O electrostatic stabilizations in the Mannich and transannular steric repulsion in the acylation step.

Computational elucidation of the mechanism and diastereocontrol in the 4-component synthesis of γ-lactams from α-cyanosuccinic anhydrides and imines

245th National Meeting (2013)

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