Directed regiochemical control in the ring expansion reactions of a substituted trans-decalone

A derivative of the Wieland-Miescher ketone can selectively be converted into either regioisomeric ring-expanded lactam. The synthesis of the diastereomeric N-α-methylbenzyl oxaziridine derivatives determines the regiochemistry of the product lactam and additionally allows the separation of a racemic substrate into regio- and enantioisomeric lactams.