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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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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cited_by cdi_FETCH-LOGICAL-c470t-68f1629e99ddeddfd5ab16aa44dc722c92da7bd5aadfc871fb16a7ed046615dc3
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container_issue 35
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container_title Tetrahedron
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creator Beňadiková, Daniela
Čurillová, Júlia
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description 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]
doi_str_mv 10.1016/j.tet.2014.06.093
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subjects 2,3-Dihydroisoxazoles
Cyanations
Dihydroxylations
Isoxazolidines
Mathematical models
Selectivity
Synthesis (chemistry)
Tetrahedrons
title 4,5-Unsubstituted 2,3-dihydroisoxazoles in the synthesis of racemic 4-substituted isoxazolidine-5-carbonitriles
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