Unusually Stable Isoxazolidinyl Epoxides: Synthesis and Reactivity in Nucleophilic Substitutions

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Authors	ZABORSKY Ondrej MALATINSKY Tomas MAREK Jaromír MONCOL Jan FISCHER Robert
Year of publication	2016
Type	Article in Periodical
Magazine / Source	European Journal of Organic Chemistry
MU Faculty or unit	Central European Institute of Technology
Citation
Web	http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201600471/abstract;jsessionid=7A316B02D70DA68F1146CBD0E83FD9BA.f04t03?systemMessage=Pay+per+view+article+purchase%28PPV%29+on+Wiley+Online+Library+will+be+unavailable+on+Saturday+11th+March+from+05%3A00-14%
Doi	http://dx.doi.org/10.1002/ejoc.201600471
Field	Organic chemistry
Keywords	Heterocycles; Epoxides; Ring opening; Nucleophilic substitution; Oxidation; Diastereoselectivity
Description	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.
Related projects:	CEITEC - open access