Ring-selective syntheses of homochiral oxepanes and tetrahydropyrans from carbohydrates via intramolecular nitrone or nitrile oxide cycloadditions

Tony K.M. Shing; Wing Chuen Fung; Ching Hung Wong

doi:10.1039/C39940000449

Ring-selective syntheses of homochiral oxepanes and tetrahydropyrans from carbohydrates via intramolecular nitrone or nitrile oxide cycloadditions

Tony K.M. Shing, Wing Chuen Fung, Ching Hung Wong

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

45 Citations (Scopus)

Abstract

Intramolecular 1,3-dipolar cycloadditions of nitrones formed from 3-O-allyl-1,2-O-isopropylidene-α-D-pentodialdofuranoses afford oxepanes or tetrahydropyrans selectively whereas the intramolecular cycloadditions of nitrile oxides derived from the same aldehydes give exclusively tetrahydropyrans.

Original language	English
Pages (from-to)	449-450
Number of pages	2
Journal	Journal of the Chemical Society, Chemical Communications
Issue number	4
DOIs	https://doi.org/10.1039/C39940000449
Publication status	Published - 1994 Dec 1

ASJC Scopus subject areas

Molecular Medicine

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abstract = "Intramolecular 1,3-dipolar cycloadditions of nitrones formed from 3-O-allyl-1,2-O-isopropylidene-α-D-pentodialdofuranoses afford oxepanes or tetrahydropyrans selectively whereas the intramolecular cycloadditions of nitrile oxides derived from the same aldehydes give exclusively tetrahydropyrans.",

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