Abstract
The synthesis of new N‐carbamoyl‐substituted isoxazolidine‐4,5‐diols and their 4,5‐anhydro analogues, isoxazolidinyl epoxides, is described. The 4,5‐unsubstituted 2,3‐dihydroisoxazole starting materials reacted directly with potassium osmate/4‐methylmorpholine N‐oxide and 3,3‐dimethyldioxirane, respectively. All addition reactions proceeded with excellent anti selectivity with respect to the substituent at C‐3. The obtained isoxazolidinyl epoxides as well as benzoylated isoxazolidine‐4,5‐diols were subjected to nucleophilic substitution reactions with various nucleophiles. 4‐Hydroxyisoxazolidines with chlorine, methoxy, and azide substituents bound to C‐5 were prepared in moderate to good yields. In terms of chemical stability, the discussed isoxazolidinyl epoxides can be isolated and stored for a long time.
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