Intramolecular Nitrile Oxide−Alkene Cycloaddition of Sugar Derivatives with Unmasked Hydroxyl Group(s)

Intramolecular nitrile oxide−alkene cycloaddition (INOC) of sugar derivatives with one to four free hydroxyl group(s) is reported. The INOC reaction, using chloramine-T, in the presence of silica gel, to generate nitrile oxides from oximes, proceeded smoothly to afford five- or six-membered carbocyc...

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Bibliographic Details
Published in:Organic letters 2007-03, Vol.9 (5), p.753-756
Main Authors: Shing, Tony K. M, Wong, Wai F, Cheng, Hau M, Kwok, Wun S, So, King H
Format: Article
Language:English
Subjects:
Alkenes - chemistry
Carbohydrates - chemistry
Chloramines - chemistry
Cyclization
Hydroxylation
Lactones - chemistry
Molecular Structure
Nitriles - chemistry
Oximes - chemistry
Silica Gel
Silicon Dioxide - chemistry
Tosyl Compounds - chemistry
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Summary:Intramolecular nitrile oxide−alkene cycloaddition (INOC) of sugar derivatives with one to four free hydroxyl group(s) is reported. The INOC reaction, using chloramine-T, in the presence of silica gel, to generate nitrile oxides from oximes, proceeded smoothly to afford five- or six-membered carbocycles in good to excellent yields. This new methodology alleviates protection/deprotection steps and makes the synthetic route shorter and more efficient.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol062873p