Diastereoselective Diels-Alder reactions of nonracemic 3- and 4-amino furans bound to polystyrene. A comparison of these reactions to their solution state analogues

Abstract

The potassium enolates of the 3 and 4-amino furanones 4 and 12 have been silylated with polymer 3. The resulting polymer-bound nonracemic amino furans 5 and 11 were found to undergo the Diels-Alder reaction with a variety of dienophiles. The endo-adducts derived from methyl acrylate were both directly cleaved from the polymer and or synthetically manipulated and then cleaved from the polymer to demonstrate their formation in >99% de.