Département de chimie moléculaire

In the presence of a nonracemic stilbenediol bis(phosphite) ruthenium complex, nitrones derived from ketoesters underwent diastereoselective and enantioselective 1,3-dipolar cycloaddn. reactions with methacrolein to give formylisoxazolidinecarboxylates; using Me tert-Bu ether or toluene as the solvent or using N-benzyl or N-Me nitrones yielded the endo- and exo-cycloadducts as the major diastereomers, resp. The solvent effect was rationalized based on interactions between the methacrolein-Ru complex and its hexafluoroantimonate counteranion found using computational methods.