New synthetic methodologies: diamination and aza-diels-alder
McPherson, Lauren M.
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The quest for novel synthetic methodologies that allow for the synthesis of highly functionalized chiral "building blocks" is a challenging and medicinally important topic in organic chemistry. The Li group has made significant contributions in this area by developing efficient and cost effective asymmetric and stereoselective methodologies for the synthesis of highly functionalized nitrogen-containing chiral building blocks. The synthesis of these highly functionalized molecules requires the development of asymmetric and stereoselective methodologies, which continues to remain a daunting task for the modern synthetic organic chemist. In this thesis, two novel synthetic methodologies for the synthesis of vicinal diamines and aza-Diels-Alder products will be discussed. The synthesis of vicinal diamines from á,â-unsaturated ketones and esters will be the first methodology presented. The 1,2-diamino functionality is present in numerous naturally occurring and medicinally important compounds. Furthermore, these vicinal diamine products closely resemble the structure of naturally occurring amino acids and thus these compounds are invaluable for peptidomimetic studies, in that they can mimic both á- and â- amino acids, as well as the development of novel organocatalysts. The development of an aza-Diels-Alder reaction utilizing a novel iodo-diene will also be discussed. These reactions involve carbon-carbon bond formation and facilitate the synthesis of nitrogen-containing heterocycles. These valuable products are commonly found in modern medicines as well as a plethora of natural products.