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@article{1375172,
author = {Zaborsky, Ondrej and Malatinsky, Tomas and Marek, Jaromír and Moncol, Jan and Fischer, Robert},
article_location = {Weinheim},
article_number = {23},
doi = {http://dx.doi.org/10.1002/ejoc.201600471},
keywords = {Heterocycles; Epoxides; Ring opening; Nucleophilic substitution; Oxidation; Diastereoselectivity},
language = {eng},
issn = {1434-193X},
journal = {European Journal of Organic Chemistry},
title = {Unusually Stable Isoxazolidinyl Epoxides: Synthesis and Reactivity in Nucleophilic Substitutions},
url = {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%},
volume = {neuveden},
year = {2016}
}
TY - JOUR
ID - 1375172
AU - Zaborsky, Ondrej - Malatinsky, Tomas - Marek, Jaromír - Moncol, Jan - Fischer, Robert
PY - 2016
TI - Unusually Stable Isoxazolidinyl Epoxides: Synthesis and Reactivity in Nucleophilic Substitutions
JF - European Journal of Organic Chemistry
VL - neuveden
IS - 23
SP - 3993-4002
EP - 3993-4002
PB - WILEY-VCH
SN - 1434193X
KW - Heterocycles
KW - Epoxides
KW - Ring opening
KW - Nucleophilic substitution
KW - Oxidation
KW - Diastereoselectivity
UR - 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%
L2 - 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%
N2 - 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.
ER -
ZABORSKY, Ondrej, Tomas MALATINSKY, Jaromír MAREK, Jan MONCOL and Robert FISCHER. Unusually Stable Isoxazolidinyl Epoxides: Synthesis and Reactivity in Nucleophilic Substitutions. \textit{European Journal of Organic Chemistry}. Weinheim: WILEY-VCH, 2016, neuveden, No~23, p.~3993-4002. ISSN~1434-193X. Available from: https://dx.doi.org/10.1002/ejoc.201600471.
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