Interrupting the Nazarov Cyclization with Bromine

Autor:	Devon J. Schatz, Thomas W. Scully, Yonghoon Kwon, Frederick G. West
Rok vydání:	2016
Předmět:	Bromine 010405 organic chemistry Chemistry Organic Chemistry chemistry.chemical_element Halogenation 010402 general chemistry 01 natural sciences Medicinal chemistry 3. Good health 0104 chemical sciences Nucleophile Product (mathematics) Electrophile Organic chemistry
Zdroj:	The Journal of Organic Chemistry. 81:12494-12498
ISSN:	1520-6904 0022-3263
Popis:	The generation of dibrominated cyclopentenones via an interrupted Nazarov cyclization is reported. The installation of two bromine atoms occurs at the α and α' positions of the cyclopentenyl scaffold via successive nucleophilic and electrophilic bromination of the 2-oxidocyclopentenyl cation and its resulting enolate. Notably, the reaction proceeds with good diastereoselectivity, favoring the symmetrical product.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::fca8414b5a2daaca4402e7e138dcc5a2 https://doi.org/10.1021/acs.joc.6b02350 Zobrazit plný text záznamu