Organometallics are very versatile reagents for the formation of carbon- carbon bonds. However very few of them show at the same time a high reactivity and a good tolerance to important functional groups. The availability of a variety of such polyfunctionalized organometallics would be of considerable importance fore the planning of synthesis of complex molecules and would allow shorter and more efficient pathways. We propose to develop methodologies which will make possible the preparation of a number of polyfunctional organo-copper reagents RCu(CN)ZnI and to study the scope and the limitations of the reactivity of these and related reagents toward several organic electrophiles. Intramolecular reactions leading to ring closures as well as an asymmetric version of the reaction will be examined and applications directed toward the synthesis of biologically active molecules will be investigated. Furthermore we will examine a new approach to highly functionalized zinc organometallics through substitution reactions at halomethyl zinc derivatives, a new stereocontrolled approach to aldol-type products as well as a method for the distereoselective synthesis of organolithium compounds by using functionalized allylic organometallics. We believe that our studies will give access to several new classes of highly functionalized organometallics which will be useful for the synthesis of organolithium compounds by using functionalized allylic organometallics. We believe that our studies will give access to several new classes of highly functionalized organometallics which will be useful for the synthesis of complex polyfunctional molecules.
