Domino reactions that combine an azido-Schmidt ring expansion with the Sakurai reaction

This thesis describes the development and mechanistic study of two-component Sakurai-Schmidt reactions. Simple substrates such as allyl silanes and appropriate azidoenones have been used to synthesize five different lactams using the developed protocol. Both mono- and bicyclic lactams were synthesized using this methodology. In order to study the stereoselectivity of this process, the reaction has also been performed by first isolating the Sakurai adducts and then subjecting them to the Schmidt reaction. It was found that these two different methods have a an effect on the selectivity of the products formed. The effect of using methanol and the bulkier alcohol t-butanol on some of the reactions has also been investigated.