Date of Award
Open Access Honors Thesis
Bachelor of Science (BS)
2-piperidinone (δ-lactam), a bio-interesting nitrogen-containing six-membered ring compound, has attracted much interest from researchers both in synthetic and medicinal chemistry. Polysubstituted piperidine derivatives, such as the δ-lactam, serve as a synthon for numerous biologically relevant structures and pharmaceutical agents. A novel one-pot asymmetric Michael/Mannich/Lactamization sequence promoted by recyclable fluorous bifunctional cinchona alkaloid–thiourea organocatalysts is introduced for the synthesis of polysubstituted 2-piperidinones bearing four contiguous stereocenters, one of which is a fluorinated quaternary chiral center with excellent stereoselectivities (ee up to >99%, dr up to >20:1).
Tran, Anthony P., "Recyclable Organocatalysis of One-pot Michael/Mannich/Lactamization Sequence for Asymmetric Synthesis of Fluorinated Poly-substituted 2-Piperidinones" (2015). Honors College Theses. 10.