Article

Allylation of erythromycin derivatives: introduction of allyl substituents into highly hindered alcohols.

Global Pharmaceutical Research and Development, Abbott Laboratories, 1401 Sheridan Road, North Chicago, IL 60064-6290, USA.
The Journal of Organic Chemistry (impact factor: 4.45). 12/2003; 68(23):8847-52. DOI:10.1021/jo034883z pp.8847-52
Source: PubMed

ABSTRACT Functionalized erythromycin 9-oxime derivatives are 6-O-allylated under mild conditions using substituted allyl tert-butyl carbonates under palladium(0) catalysis. This allylation works well where traditional ether-forming protocols function poorly. Allyl tert-butyl carbonates provide higher yields in this reaction than lesser substituted carbonates such as ethyl or isopropyl. Aryl-substituted allyl carbonates or carbamates may be employed as well and, when used, produce trans-olefinic products.

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Keywords

allyl tert-butyl carbonates
 
allylation works
 
Functionalized erythromycin 9-oxime derivatives
 
higher yields
 
isopropyl
 
mild conditions
 
traditional ether-forming protocols function
 
trans-olefinic products
 

Eric J Stoner