A New Synthesis of Highly Functional Nitrones through a Nitrosoketene Intermediate and Their Use for the Stereoselective Synthesis of Amino Acids

Article abstract of DOI:10.1021/jo00105a029

Reaction of 5-isonitroso-2,2-dimethyl-1,3-dioxane-4,6-dione with various ketones under reflux in toluene gives 3-oxazolin-5-one 3-oxides (cyclic nitrones) via a nitrosoketene intermediate generated from the isonitroso derivative.The cyclic nitrones can be used for the stereoselective <3 + 2> dipolar cycloaddition to electron-rich olefins under high pressure to produce fused isoxazolidines.These isoxazolidines, in turn, are versatile intermediates for the stereoselective preparation of substituted α-amino acids.