Sulfoxonium ylides can react with nitrosoarenes to produce nitrones under catalyst-free conditions; however, prolonged heating conditions are required. In this study, MgBr 2 •OEt 2 was employed to promote the reaction of nitroso compounds with α-carbonyl sulfoxonium ylides, producing corresponding nitrones. When conducted in the presence of magnesium salts, the one-pot tandem nitrone formation/1,3-dipolar cycloaddition to allyl alcohol afforded the corresponding isoxazolidines diastereoselectively. Furthermore, the magnesium salt of tartramide was used to realize chiral induction in the 1,3-dipolar cycloaddition reaction, resulting in the optically active isoxazolidine. Our approach represents a promising one-pot strategy for synthesizing optically active isoxazolidines.
Maegawa et al. (Sat,) studied this question.