4,5-Unsubstituted 2,3-dihydroisoxazoles in the synthesis of racemic 4-substituted isoxazolidine-5-carbonitriles

The synthesis of novel types of the 4-hydroxy- and 4-bromosubstituted isoxazolidines is described. Dihydroxylation reactions of 4,5-unsubstituted 2,3-dihydroisoxazoles proceed from the less hindered side and provide the major 3,4-trans-isoxazolidine-4,5-diols in good yields. On the other hand, the h...

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Bibliographic Details
Published in:Tetrahedron 2014-09, Vol.70 (35), p.5585-5593
Main Authors: Beňadiková, Daniela, Čurillová, Júlia, Lacek, Tomáš, Rakovský, Erik, Moncol', Ján, Doháňošová, Jana, Fischer, Robert
Format: Article
Language:English
Subjects:
2,3-Dihydroisoxazoles
Cyanations
Dihydroxylations
Isoxazolidines
Mathematical models
Selectivity
Synthesis (chemistry)
Tetrahedrons
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Summary:The synthesis of novel types of the 4-hydroxy- and 4-bromosubstituted isoxazolidines is described. Dihydroxylation reactions of 4,5-unsubstituted 2,3-dihydroisoxazoles proceed from the less hindered side and provide the major 3,4-trans-isoxazolidine-4,5-diols in good yields. On the other hand, the hydroxybromination reaction of the model 3-phenyl-2,3-dihydroisoxazole predominantly proceeds with 3,4-cis selectivity. Isoxazolidine-5-carbonitriles have been prepared from isoxazolidines possessing a good leaving group at C5 by treatment with TMSCN in the presence of TMSOTf. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2014.06.093