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Amino Alcohols in Organocatalysed Acylation and Deacylation: The Effect of Dialkylamino Substituents on the Rate

✍ Scribed by Ludger A. Wessjohann; Mingzhao Zhu

Publisher: John Wiley and Sons
Year: 2008
Tongue: English
Weight: 374 KB
Volume: 350
Category: Article
ISSN: 1615-4150
DOI: 10.1002/adsc.200600491

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✦ Synopsis

Abstract

In alcohols and esters, a neighbouring dialkylamino group can enhance the reactivity towards acylation and deacylation, respectively, that is, such amino alcohols can act as transacylation catalysts like DMAP. This effect is dependent on the number of (carbon) spacer atoms, flexibility of the molecule and the presence and position of further heteroatoms. Based on this effect, the site selective acylation and deacylation of desmycosin, a macrocycle antibiotic possessing an amino sugar moiety, is described.

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