Stereoselective Cyclopropanation to Homoquinones from Phenacyl Carbenes Obtained through Quinone-Electrogenerated Bases

Autor:	Fructuoso Barba, Kaouthar Hamrouni, Mohamed Lamine Benkhoud, Belen Batanero
Rok vydání:	2017
Předmět:	Reaction mechanism 010405 organic chemistry Chemistry Cyclopropanation Organic Chemistry 010402 general chemistry Photochemistry Phenacyl 01 natural sciences Medicinal chemistry Cycloaddition 0104 chemical sciences Quinone chemistry.chemical_compound Yield (chemistry) Stereoselectivity Carbene
Zdroj:	The Journal of Organic Chemistry. 82:6778-6785
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.7b00925
Popis:	A series of new (E) and (Z)-benzoyl-homoquinones have been prepared in good yield by the parent quinone-electrogenerated base (EGB) in the presence of α-bromoacetophenones or α-bromopropiophenone. The EGB, obtained when electrolysis of p-benzoquinone, or 1,4-naphthoquinone, is carried out at the reduction potential of their first voltammetric peak, conducted to electrogenerated phenacyl carbenes after halide evolution on the first obtained bromo-enolates. The stereoselectivity of the [2 + 2]cycloaddition of the carbene to the quinoid substrate is highly dependent on the electrode nature. Reaction mechanism proposal is discussed.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::c58195b1c114e03aab651c9a5a4dca80 https://doi.org/10.1021/acs.joc.7b00925 Zobrazit plný text záznamu