New Electrophiles for the Catalytic, Asymmetric "Interrupted" Feist-Bénary Reaction

Abstract

Many of the molecules essential for life are inherently dissymmetric. Enantioselective organocatalysis-the synthesis of enantioenriched products from achiral or racemic starting materials through the use of small organic catalysts-can provide inexpensive, environmentally friendly access to such compounds. This thesis describes efforts toward the development of new organocatalytic methodologies for the enantioselective synthesis of a particularly important class of molecules, highly functionalized dihydrofuranoids, through the catalytic, asymmetric "interrupted" Feist-Bénary (IFB) reaction. Were I to appropriately express my gratitude towards everyone to whom I owe thanks, these acknowledgements would extend far beyond the page allotted to them. With that said, and my sincerest apologies to those who I fail to mention, I'd like to begin by thanking my advisor, Professor Michael Calter. At some point during the fall of 2013, I attempted to count the number of times I said "Professor Calter, do you have a minute?" during the course of a single week. I lost track by Tuesday afternoon. I cannot overstate how much Professor Calter's perpetual willingness to take time out of his day to answer my countless questions has meant to me. Thank you, Professor Calter, for giving me the opportunity to work in your lab, for your constant guidance, and for all you've taught me over the last three years. Next, I'd like to thank the members of Calter lab past and present