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Trends in Organic Chemistry   Volumes    Volume 8 
Abstract
Novel reactions of isobutylaluminium reagents in carbohydrate chemistry
Pierre Sinay, Alan James Pearce
Pages: 129 - 135
Number of pages: 7
Trends in Organic Chemistry
Volume 8 

Copyright © 2000 Research Trends. All rights reserved

ABSTRACT

Here we summarise our recent developments in the field of selective reactions of carbohydrates promoted by isobutylaluminium reagents.  The triisobutylaluminium (TIBAL) promoted rearrangement of carbohydrate based vinyl acetals (hex-5-enopyranosides) provides a powerful and versatile method for the preparation of highly functionalised enantiomerically pure cyclohexanes.  TIBAL and diisobutylaluminium (DIBAL) also promote the regioselective de-O-benzylation of readily available protected sugars providing direct access to selectively protected carbohydrates.  The scope and limitations of these highly selective reactions are described.

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