Diastereoselective Synthesis of 2-Cyanomethyl-3-hydroxy-5-iodomethyltetrahydrofuran from Isoxazolines by Iodoetheration

Diastereoselective Synthesis of 2-Cyanomethyl-3-hydroxy-5-iodomethyltetrahydrofuran from Isoxazolines by Iodoetheration

Abstract Diastereoselective 1,3-dipolar cycloaddition reaction of nitrile oxides with 1,5-hexadien-3-ol afforded SYN-5-(1-hydroxy-3-butenyl)isoxazolines, which underwent iodoetheration by iodine monochloride to give 2-cyanomethyl-3-hydroxy-5-iodomethyl­tetrahydrofuran with diastereoselectivity. The...

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Veröffentlicht in:Synlett 2002-10, Vol.2002 (10), p.1691-1693
Hauptverfasser: Kim, Hyoung Cheul, Woo, Seung Woo, Seo, Min Jung, Jeon, Dong Ju, No, Zaesung, Kim, Hyoung Rae
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Sprache:eng
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Zusammenfassung:Abstract Diastereoselective 1,3-dipolar cycloaddition reaction of nitrile oxides with 1,5-hexadien-3-ol afforded SYN-5-(1-hydroxy-3-butenyl)isoxazolines, which underwent iodoetheration by iodine monochloride to give 2-cyanomethyl-3-hydroxy-5-iodomethyl­tetrahydrofuran with diastereoselectivity. The relative stereo­chemistry of iodomethyl group varied depending on both the 3-substituents and the hydroxy protecting groups.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2002-34245