Additional reactions of sugar oximes, nitrite oxides and hydroximolactones
- 1 January 1991
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- Vol. 23 (11) , 2801-2809
- https://doi.org/10.1039/p19910002801
Abstract
Reaction of sugar oximes with dimethyl acetylenedicarboxylate gave chiral isoxazolines bearing a sugar moiety. Sugar nitrite oxides reacted with 1,3-dipolarophiles to afford the corresponding isoxazoles bearing a sugar moiety. Sugar hydroximolactones underwent a tandem Michael addition-1,3-dipolar cycloaddition by reaction with Michael acceptors to give the corresponding spiro sugar isoxazolidines. An X-ray crystallographic structure determination of (3S,5R,7R,8R,9R)-3-acetyl-8,9-isopropylidenedioxy-l-(3-oxobutyl)-7-trityloxymethyl-2,6-dioxa-1-azaspiro[4.4]nonane has been performed.Keywords
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