Physical Sciences and Mathematics Commons^™

Development Of Regio- And Diastereoselective Samarium (Ii) Iodide Mediated Allylic Benzoate Reductions, Trevor Stockdale

WWU Graduate School Collection

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.