Cope rearrangements and lactol formations: Indium metal promoted couplings with versatility

ORGN 570

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 controlling the structure of natural products and synthetic templates. Indium metal has historically shown to add preferentially to unsaturated carbonyl moieties with 1,2- preference over a 1,4-addition pathway. This poster will address studies in our laboratory revealing that indium promoted couplings to propargyl aldehydes may be controlled to give the 1,2-, or 1,4-addition product. Slight modifications to these conditions also allow formation of the 6-membered ring lactol as shown in Scheme 1.