Enantioselective access to benzannulated spiroketals using a chiral sulfoxide auxiliary

Autor:	Harry R. M. Aitken, Daniel P. Furkert, Jonathan G. Hubert, James M. Wood, Margaret A. Brimble
Rok vydání:	2013
Předmět:	Molecular Structure Chemistry Stereochemistry Organic Chemistry Quinones Diastereomer Enantioselective synthesis Benzene Stereoisomerism Sulfoxide Ring (chemistry) Biochemistry chemistry.chemical_compound Safrole Spiro Compounds Physical and Theoretical Chemistry Enantiomer Furans
Zdroj:	Organic & Biomolecular Chemistry. 11:5147
ISSN:	1477-0539 1477-0520
Popis:	This article describes our efforts to develop an asymmetric synthesis of bisbenzannulated spiroketals using a chiral sulfoxide auxiliary. Our primary focus was on the synthesis of the 3H-spiro[benzofuran-2,2'-chroman] ring system, the spirocyclic core of the rubromycin family. Our strategy employed the use of lithium-halogen exchange on a racemic bromospiroketal in order to attach a chiral sulfoxide, thus producing two diastereomers. The diastereomers were separable, enabling isolation of each spiroketal enantiomer. Subsequent cleavage of the sulfoxide group from each diastereomer yielded the respective parent spiroketal in high enantiopurity.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::e04848e00af50d22db64f265c6335d02 https://doi.org/10.1039/c3ob41065j Zobrazit plný text záznamu