Indium-promoted additions to propargyl aldehydes: Mechanistic studies into Michael additions versus Cope rearrangements

ORGN 97

Thomas M. Mitzel, Department of Chemistry, Trinity College, 300 Summit Street, Hartford, CT 06106 and Annie Troutman, Chemistry, Trinity College, 300 Summit Street, Hartford, CT 06106.

 

Formation and control of carbon-carbon bonds are an essential part of organic synthesis. Indium promotes these types of formations and its utilization has advantages over traditionally used metals. Historically, Indium metal has shown a preference in adding to carbonyl moieties in a 1,2- rather than a 1,4-fashion.  In the system shown below, Michael-type of additions have been witnessed.  This poster will focus on the mechanistic pathway leading to formation of these "Michael Products" by either 1,4-addition or Cope Rearrangement and use of this technology in formation of ene-diyne molecules.