Chemoselective Access to γ-Ketoesters with Stereogenic Quaternary α-Center or γ-Keto Nitriles by Aerobic Reaction of α-Cyanoesters and Styrenes

Autor:	Ze-Long Yu, Xian-Jin Wang, Song-Lin Zhang
Rok vydání:	2017
Předmět:	Olefin fiber Aerobic reaction 010405 organic chemistry Metal salts Chemistry Organic Chemistry 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences Stereocenter Adduct Organic chemistry Physical and Theoretical Chemistry Stoichiometry
Zdroj:	Organic Letters. 19:3139-3142
ISSN:	1523-7052 1523-7060
DOI:	10.1021/acs.orglett.7b01264
Popis:	Chemoselective access to either γ-ketoesters with a quaternary all-carbon α-stereogenic center or γ-keto nitriles is described by copper-catalyzed aerobic reaction of styrenes with α-cyanoesters. Formal oxo-enolation or oxo-cyanomethylation of styrenes is achieved via a sequence of addition of enolate (or cyanomethyl) radical to olefin and oxidation of the resulting radical adduct. This method starts from abundant and cheap feedstock under aerobic conditions, without any prefunctionalization or the production of stoichiometric metal salts waste, making it very attractive for practical use.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::745819d28f27c863f8eb4caf30eb3e72 https://doi.org/10.1021/acs.orglett.7b01264 Zobrazit plný text záznamu