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Unusually Stable Isoxazolidinyl Epoxides: Synthesis and Reactivity in Nucleophilic Substitutions
Author(s) -
Záborský Ondrej,
Malatinský Tomáš,
Marek Jaromír,
Moncol Ján,
Fischer Róbert
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600471
Subject(s) - chemistry , nucleophile , dimethyldioxirane , substituent , selectivity , epoxide , azide , reactivity (psychology) , nucleophilic substitution , chlorine , organic chemistry , sodium azide , yield (engineering) , medicinal chemistry , catalysis , medicine , materials science , alternative medicine , pathology , metallurgy
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.