Efforts toward the synthesis of a new generation of modular, highly diastereoselective, and cleavable oxadiazinone chiral auxiliaries

ORGN 701

Jesse Wolfe, jawolfe@ilstu.edu, Chemistry, Illinois State University, campus box 4160, Normal, IL 61790-4160 and Shawn R. Hitchcock, hitchcock@ilstu.edu, Department of Chemistry, Illinois State University, Campus Box 4160, Normal, IL 61790-4160.
Oxadiazinones have been successfully used in the asymmetric aldol addition reaction as stoichiometric chiral auxiliaries. However, there is a limitation in their use as the aldol adducts that form do not, in general, readily cleave from the oxadiazinone template under either basic or acidic conditions. The oxadiazinones undergo endocyclic cleavage to generate hydrazides that are difficult to further hydrolyze. This presentation will focus on the development of new class of oxadiazinones where high diastereoselectivity is sought as well as improved ease of cleavage. The past examples of oxadiazinone auxiliaries where derived from ephedrine, norephedrine and beta-aminoalcohols derived from phenylalanine. The current work employs 1-phenyl-1,2-ethanediol as a starting material. The hydrazine component of the oxadiazine is then assembled via carbazate chemistry rather than nitrosamine chemistry. This poster will cover the efforts that have been conducted thus far to launch this new family of oxadiazinones as effective templates for conducting asymmetric syntheses.