ENE REACTIONS OF METHYLIDENE THIAZOLIDINES

Abstract

This thesis describes the synthesis of seven new racemic molecules from methylidene thiazolidines reacting with two enophiles, N-phenylmaleimide and ethyl glyoxylate. The synthesis of these molecules was achieved through the ene reaction under thermal conditions, resulting in an adduct containing a single chiral carbon. This is foundational work in exploration of ene reactions of the methylidiene thiazolidines used in this work with different enophiles and eventually asymmetric catalysis to synthesize chiral compounds, such as non-natural amino acids. Chapter 1 of this thesis describes the ene reaction and the various molecules that were synthesized via an ene reaction. It also describes very recent chemistry and applications of thiazolidines and their derivatives. Chapter 2 of this thesis reports the exploratory attempts of the ene reactions with 6 different methylidene thiazolidines and N-phenylmaleimide, which resulted in successful synthesis of the products in low yields. It then describes what experimental changes needed to be made to optimize the yields. Another reaction described is reacting one of methylidene thiazolidines with ethyl glyoxylate, and two different experimental methods were used. One method showed that the product was successfully synthesized using pure ethyl glyoxylate, and another method shows that synthetic ethyl glyoxylate can be used to successfully synthesize the product. Chapter 3 of this thesis has the experimental procedures used to synthesize each new molecule and the characterization data for each new molecule.