title: Allylation of erythromycin derivatives: introduction of allyl substituents into highly hindered alcohols.
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.
authors: Global Pharmaceutical Research and Development, Abbott Laboratories, 1401 Sheridan Road, North Chicago, IL 60064-6290, USA. eric.stoner@abbott.com
authors: Eric J
authors: EJ
authors: Stoner
authors: Matthew J
authors: MJ
authors: Peterson
authors: Michael S
authors: MS
authors: Allen
authors: John A
authors: JA
authors: DeMattei
authors: Anthony R
authors: AR
authors: Haight
authors: M Robert
authors: MR
authors: Leanna
authors: Subhash R
authors: SR
authors: Patel
authors: Daniel J
authors: DJ
authors: Plata
authors: Ramiya H
authors: RH
authors: Premchandran
authors: Michael
authors: M
authors: Rasmussen
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D000478:Alkylation; D004917:Erythromycin / Q000737:chemistry*
chemical_list: D000438:Alcohols; D004917:Erythromycin