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Master of Science (MS)
O'Neil, Gregory (Gregory W.)
Vyvyan, James R.
Gilbertson, John D.
Herein, we report a regio- and diastereoselective samarium mediated allylic benzoate reduction. The reaction can achieve high yields, regioselectivity, and diastereoselectivity, however there appear to be many factors influencing the outcome: proton sources, alkene geometry, chelating group length, relative stereocenter positioning, and stereocenter identity. These substrate parameters were looked at in-depth which ultimately led to several conclusions about optimized substrates. For instance, experiments indicate that the reaction proceeds through a bicyclic organosamarium species followed by intramolecular protonation from samarium bound water.
Samarium diiodide, regioselective, diastereoselective, organosamarium, stereoselective synthesis
Western Washington University
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Stockdale, Trevor, "Development of Regio- and Diastereoselective Samarium (II) Iodide Mediated Allylic Benzoate Reductions" (2018). WWU Graduate School Collection. 708.