The research interests of our group lie in the development of new synthetic methodology using novel main-group organometallic chemistry. A major focus of our effort involves investigation of the synthetic utility of unsaturated organolithiums and related Group 1 organometallics. These reactive intermediates, which we have found may be prepared in virtually quantitative yield by low – temperature lithium – iodine exchange between t -butyllithium ( t -BuLi) and an appropriate organoiodide, undergo regiospecific and highly stereoselective cyclization upon warming. The high degree of stereocontrol inherent in these anionic cyclizations has led to development of one step, stereoselective syntheses of simple natural products and tandem – cyclization strategies for the preparation of bicyclic and polycyclic structures. A brief, schematic survey of some of our work in the area of intramolecular carbolithiation is presented below.
We are currently exploring enantioselective routes to a variety of cyclic molecules based asymmetric cyclization of achiral olefinic organolithiums that are controlled by a stereogenic lithium. The practical problems associated with the use of large quantities of organolithium reagents in process chemistry are being addressed by development of a highly atom-economical isomerization, catalytic in alkyllithium , that serves to convert a variety of unsaturated organoiodides to their cyclic isomers in high yield.
In parallel with our synthetic efforts, we are actively engaged in mechanistic, spectroscopic and computational investigations of the fundamental structure and reactivity of Group 1 organometallics.
Research in the Bailey Group 
