DTBB-Catalysed Lithiation of Acenaphthylene and Reaction with Carbonyl Compounds

Autor:	Cecilia Gómez, Miguel Yus, Victor J. Lillo
Rok vydání:	2008
Předmět:	Organic Chemistry chemistry.chemical_element Cyclohexanone Cyclopentanone Acenaphthylene Medicinal chemistry Catalysis Hydrolysis chemistry.chemical_compound chemistry Lithium Stereoselectivity Tetrahydrofuran
Zdroj:	Synthesis. 2008:1241-1248
ISSN:	1437-210X 0039-7881
DOI:	10.1055/s-2008-1042943
Popis:	The reaction of acenaphthylene with an excess of lithium powder and a catalytic amount of DTBB (7.5 mol%) in tetrahydrofuran at -70 °C followed by treatment with a carbonyl compound [Me 2 CO, Et 2 CO, I-Pr 2 CO, ( C-C 3 H 5 ) 2 CO, cyclopentanone, cyclohexanone, 2-adamantanone, Ph 2 CO, T-BuCHO] leads, after hydrolysis with water, to an easily chromatographically separable mixture of two products resulting from disubstitution at the 1,2-positions and monosubstitution at the 1-position, respectively. The reaction is regio- and stereoselective, so in the case of the disubstituted compounds only the TRANS-diastereomers are obtained.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::09ca84877a18f2efc7fcb1107493ff4f https://doi.org/10.1055/s-2008-1042943 Zobrazit plný text záznamu