Date of Award
Program or Major
Master of Science
Synthetic sequences to prepare gamma-methoxy beta-keto imides and malonyl diimides were investigated in an effort to expand the scope of the tandem zinc-mediated chain extension aldol reaction. The chain extension-aldol reaction of the gamma-methoxy beta-keto imide proceded smoothly, although low stereoselectivity of the reaction was observed. The chain extension of malonyl diimides were slow when compared to traditional substrates. The chain extension-aldol reaction of malonyl diimides provided gamma-lactones with moderate yield and selectivity in a one-pot reaction sequence.
Due to the extended chain extension reaction times, reduction of aldehydes was observed during attempted aldol reactions. A chain extension aldol protocol, specific for the application to malonyl diimides, was developed to reduce the appearance of products resulting from the reduction of the respective aldehyde.
Henderson, Timothy J., "Tandem zinc-carbenoid mediated chain extension-aldol chemistry of beta-carbonyl imides" (2009). Master's Theses and Capstones. 480.