Synthesis of a new class of novel chiral auxiliaries: The triazinones

ORGN 153

Jonathan A Groeper, jagoep@yahoo.com and Shawn R. Hitchcock, hitchcock@ilstu.edu. Department of Chemistry, Illinois State University, 10 Willedrob Unit 6, Bloomington, IL 61701
Oxadiazinones are structurally novel chiral complexes that have been shown to afford high diastereoselectivity in the asymmetric aldol reaction. This heterocyclic system has had the recurring problem of the lack of consistency in the hydrolytic cleavage of the aldol adducts. We sought to modify the design of the original oxadiazinone in an attempt to enhance the hydrolysis. This gave rise to the to a design change, i.e. the synthesis of a new class of chiral auxiliaries that are known as triazinones. The synthesis of this triazinone will provide a new heterocyclic system that may offer a superior means of conducting the cleavage of the aldol adducts. This poster will illustrate the attempts made thus far concerning the synthesis of the enantiomerically enriched triazine heterocyclic system derived from ephedrines as well as the efforts made in streamlining the process to enhance efficiency.