ChemInform Abstract: Catalytic Applications of F8BINOL: Asymmetric Oxidation of Sulfides to Sulfoxides

Autor:	Subramanian Pandiaraju, Andrei K. Yudin, L. James P. Martyn
Rok vydání:	2000
Předmět:	chemistry.chemical_classification Sulfide Absolute configuration chemistry.chemical_element General Medicine Medicinal chemistry Catalysis chemistry.chemical_compound chemistry Electrophile Fluorine Organic chemistry Hydrogen peroxide Chiral induction Titanium
Zdroj:	ChemInform. 31
ISSN:	1522-2667 0931-7597
DOI:	10.1002/chin.200043109
Popis:	The effect of fluorine substitution at the 5, 5′, 6, 6′, 7, 7′, 8 and 8′ positions of 2,2′-dihydroxy-1,1′-binaphthyl (BINOL) on its catalytic activity in titanium-mediated sulfide oxidation with tert-butyl hydrogen peroxide and cumyl hydrogen peroxide was examined. Introduction of fluorines into the BINOL scaffold was found to increase the electrophilic character of the Lewis acidic titanium center of the catalyst. Moreover, under otherwise identical conditions, BINOL and 5,5′,6,6′,7,7′,8,8′-octafluoro-2,2′-dihydroxy-1,1′-binaphthyl (F8BINOL) of the same absolute configuration led to opposite sense of chiral induction in the sulfoxidation process.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::4414caed0e796582be075291c7bc81b2 https://doi.org/10.1002/chin.200043109 Zobrazit plný text záznamu Plný text