Allylation of Erythromycin Derivatives: Introduction of Allyl Substituents into Highly Hindered Alcohols

Autor:	Anthony R. Haight, John Demattei, Michael Rasmussen, M. Robert Leanna, Daniel J. Plata, Michael S. Allen, Subhash R. Patel, Eric J. Stoner, Matthew J. Peterson, Ramiya H. Premchandran
Rok vydání:	2003
Předmět:	Steric effects Alkylation Chemistry Organic Chemistry chemistry.chemical_element Alcohol Oxime Chemical synthesis Erythromycin Catalysis chemistry.chemical_compound Alcohols Organic chemistry Isopropyl Palladium
Zdroj:	The Journal of Organic Chemistry. 68:8847-8852
ISSN:	1520-6904 0022-3263
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::2b5573f250d7a5933e4db51397e14c4a https://doi.org/10.1021/jo034883z Zobrazit plný text záznamu