TY - JOUR TI - New approaches to the synthesis of heterocyclic molecules DO - https://doi.org/doi:10.7282/T3N87DZX PY - 2018 AB - Whether found in nature or made in the lab, small fused-ring heterocyclic molecules have found many medicinal applications. Making these molecules by building up structural complexity in a cheap and efficient manner is a driving force in organic synthesis, particularly when trying to gain access to a single enantiomer of the product. A number of synthetic approaches make use of stoichiometric and costly reagents, and involve multiple changes in the oxidation state of the product. Many of the enantioselective approaches rely on inefficient chiral auxiliaries or recrystallization techniques. This dissertation presents a new enantioselective approach to the synthesis of important lactam products, one that makes use of anion-binding by a thiourea organocatalyst to stabilize the ion pair intermediates. Enantioenriched gamma- and delta-lactams have been prepared by this approach. A method by which to synthesize useful N,S-acetals directly by combining their thiol and amine precursors, and which requires just a catalytic amount of organic acid, is also disclosed. The reaction mechanisms of these novel transformations are also explored. KW - Chemistry and Chemical Biology KW - Heterocyclic compounds KW - Chemistry, Organic LA - eng ER -