The Versatile Reactivity of Oximes with Vinyl Boronic Acids and Development of 4-Phosphono-beta-Lactams

This thesis is divided into two parts. Part I consists of two chapters which describe the tunable reactivity of oximes with alkenyl boronic acids towards C--N versus C--O bond formation. Part II has one chapter which demonstrates the development of novel phosphono-â- lactams.;Chapter 1 describes the copper-mediated etherification reaction of benzophenone oxime with alkenyl boronic acids. The synthetic utility of O-alkenyl oximes as precursors to alpha-imino aldehydes is also illustrated. Chapter 2 demonstrates a new route to highly substituted pyridine heterocycles through the thermal rearrangement of N-vinyl nitrones. The chapter provides a discussion on the preparation of N-vinyl nitrones from chalcone oximes, as well as the scope and proposed mechanistic pathway for their rearrangement.;Chapter 3 reviews the biological relevance of beta-lactam-containing compounds and discusses classical synthetic methods. The development of an efficient synthesis of 4-phosphono- beta-lactams and the design of novel 4,5- and 4,6-fused ring systems are demonstrated.