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Regiocontrol of nitrile oxide cycloadditions to allyl alcohols. Synthesis of 4-substituted and 4,4-disubstituted 5-hydroxymethyl-2-isoxazolines

✍ Scribed by Shuji Kanemasa; Masaki Nishiuchi; Eiji Wada


Publisher
Elsevier Science
Year
1992
Tongue
French
Weight
290 KB
Volume
33
Category
Article
ISSN
0040-4039

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✦ Synopsis


The well established high synthetic utility of 2?-isoxazolines is due to their synthetic equivalency of a wide variety of important functionalized building blocks such as P-hydroxy ketones+ fi-amino alcohols, cr,punsaturated ketones, and related functionalities.'

Nitrile oxide cyclctaddition offers the most useful access IO 2isoxnzoline skeletons in which one carbon-carbon bond forming process is involved. Cycloadc-!itions of niuile


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## Abstract Three isomeric monoadducts 2aA, 2aB, and 2aC of fullerene‐70 with 2,4,6‐trimethoxybenzonitrile oxide 1a were synthesized and isolated. With a combination of FAB‐MS, ^13^C‐ and ^1^H‐NMR spectroscopy the structure of the orientational and regioisomers could be assigned. A precise X‐ray st