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Synthesis of 1,2,3‐Triazoles Bearing a 4‐Hydroxyisoxazolidine Moiety from 4,5‐Unsubstituted 2,3‐Dihydroisoxazoles
Author(s) -
Štadániová Radka,
Sahulčík Michal,
Doháňošová Jana,
Moncol Ján,
Janotka Ľuboš,
Šimoničová Kristína,
Messingerová Lucia,
Fischer Róbert
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000737
Subject(s) - chemistry , moiety , cycloaddition , azide , substituent , trimethylsilyl azide , alkyne , sodium azide , triazole , ring (chemistry) , stereoselectivity , medicinal chemistry , organic chemistry , stereochemistry , catalysis
A synthetic approach towards new 1,2,3‐triazoles bearing the 3‐hydroxymethylated 4‐hydroxyisoxazolidine moiety has been described. The strategy has relied on dihydroxylation and epoxidation reactions of 4,5‐unsubstituted 2,3‐dihydroisoxazoles, allowing the introduction of the hydroxy group at the isoxazolidine ring in a trans stereoselective manner with respect to the substituent at C‐3 carbon atom. The requisite 5‐azidoisoxazolidines have been prepared from activated isoxazolidines possessing a good leaving group at C‐5 carbon atom by treatment with trimethylsilyl azide and Lewis acid (isoxazolidinyl benzoates) or with sodium azide (chloroisoxazolidines). The 1,2,3‐triazole moiety has been synthesized through copper(I)‐catalyzed azide‐alkyne cycloaddition.