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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 a Robert FISCHER. Unusually Stable Isoxazolidinyl Epoxides: Synthesis and Reactivity in Nucleophilic Substitutions. \textit{European Journal of Organic Chemistry}. Weinheim: WILEY-VCH, 2016, neuveden, č.~23, s.~3993-4002. ISSN~1434-193X. Dostupné z: https://dx.doi.org/10.1002/ejoc.201600471.
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