Novel Preparations of Alkenyl and Allenyl Beta-Aminoalkyl Sulfur Derivatives for Probing Intramolecular Cyclizations

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Kulak, Monika
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University of Guelph

Research efforts focusing on organosulfur compounds have had wide implications in the understanding of organic synthetic reactions. Nevertheless, there are still many areas to be studied, such as the stereoselectivity of sulfur mediated cyclizations, particularly those pertaining to the cis forms of 1- alkenyl β-aminoalkyl sulfoxides and sulfones. The synthesis of this small family of compounds is proposed to take place through the manipulation of Boc-protected L-amino acids. Hence, the main goal of this study was to explore the intramolecular cyclizations of cis-1-alkenyl β-aminoalkyl sulfoxides and sulfones, and various strategies are provided here in order to accomplish their synthesis in the most cost and time efficient manner. To add, the allenyl sulfenate functional group is considered to be an unknown reactive species and its substitution chemistry remains unexplored. Therefore, a second goal of this study was to generate transient allenyl sulfenates that can be used in the preparation of allenyl sulfoxides and from there, a series of new 1, 4-thiazines. For now, the allenyl sulfoxides were formed and preliminary trials for the formation of allenyl sulfenates conducted. Some leeway has been developed into the conditions and reactivity patterns pertaining to the generation chemistry of allenyl sulfenates. Further investigations as well as detailed computational results are required. It was observed that the sulfones bearing a cis alkene demonstrate little selectivity during cyclization. Overall, this study contributes to a better understanding of the most appropriate environment to access selected cyclic organosulfur compounds, which will then direct their further application.

Cyclizations, Intramolecular, Organosulfur, Allenyl, Sulfones, Sulfoxides, Sulfenates