A new reagent system for installation of an aryl group onto the monoacetate of 4-cyclopentene-1,3-diol

Autor:	Yuichi Kobayashi, Takayuki Ainai, Michiko Ito
Rok vydání:	2003
Předmět:	Aryl Organic Chemistry Diol Regioselectivity Grignard reagent Biochemistry Medicinal chemistry Coupling reaction chemistry.chemical_compound chemistry Reagent Drug Discovery Cyclopentene Organic chemistry Reactivity (chemistry)
Zdroj:	Tetrahedron Letters. 44:3983-3986
ISSN:	0040-4039
DOI:	10.1016/s0040-4039(03)00777-9
Popis:	Among the three types of reagents from PhMgX (X=Br, Cl) and CuCN for phenylation of 4-cyclopentene-1,3-diol monoacetate, PhMgCl/CuCN (cat.) and Ph2Cu(CN)(MgCl)2 in THF afforded the trans-1,4-isomer efficiently (82–87% yields, 91–93% regioselectivity). Similarly, o- and p-RC6H4MgCl (R=Me, OMe, CH2CH) in combination with CuCN furnished good to excellent reactivity and regioselectivity. As an application, a three-step synthesis of dihydromultifidene was accomplished successfully.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::edf4d01529375010695fe9d0c05a37b5 https://doi.org/10.1016/s0040-4039(03)00777-9 Zobrazit plný text záznamu Full Text from ScienceDirect