Asymmetric Olefinative Conjugate Addition (AOCA): a New Tandem Transformation

The Asymmetric Allylic Substitutions (AAA) provide an invaluable synthetic tool in organic synthesis that is commonly employed for the synthesis of drugs and natural products, with high levels of regio- and stereoselectivity. Notwithstanding the widespread utilization of this reaction, certain drawbacks arise due either to the employment of precious metals or to intrinsic mechanistic constraints. In order to overcome these limitations, we developed a new tandem transformation named Asymmetric Olefinative Conjugate Addition (AOCA) for the generation of a stereocenter in α-position with respect to an internal, functionalized olefin. High yields and enantioselectivities are obtained by the use of an inexpensive and abundant copper catalyst, making this new methodology a valuable alternative to existing methods. The reaction has been optimized and the reaction scope has been evaluated within this thesis project work.