Indium promoted couplings of propargyl aldehyde moieties with 1,2- and 1,4-regioselectivity

CHED 428

Thomas M. Mitzel, Thomas.Mitzel@mail.trincoll.edu and Joe Wzorek, thomas.mitzel@trincoll.edu. Department of Chemistry, Trinity College, 300 Summit Street, Hartford, CT 06106
Formation and control of carbon-carbon bonds are an essential part of organic synthesis. The ability to also dictate regioselectivity during these formations is an important step in formation of natural products and synthetic templates. Indium metal has historically shown to add preferentially to unsaturated carbonyl moieties in a 1,2- in preference to a 1,4-addition pathway. Studies in our lab have shown that a 1,2-addition to propargyl aldehydes followed by an in situ oxy-Cope rearrangement allows synthetic flexibility to form either the 1,2- or the “1,4”-addition product. The poster will describe the mechanistic and synthetic studies behind this reaction.