The triazinones: Towards the synthesis of a new class of chiral auxiliaries

ORGN 86

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 auxiliaries that have been shown to afford high diastereoselectivity in the asymmetric aldol reaction. A recurring problem with the aldol adducts of this heterocyclic system has been in the lack of consistency in the hydrolytic cleavage. In an attempt to enhance the hydrolysis of the aldol adduct, we sought to modify the design of the original oxadiazinone. This gave rise to a design change, i.e. the synthesis of a new class of chiral auxiliaries 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.