5466-40-0Relevant academic research and scientific papers
The palladium-catalyzed aerobic kinetic resolution of secondary alcohols: Reaction development, scope, and applications
Ebner, David C.,Bagdanoff, Jeffrey T.,Ferreira, Eric M.,McFadden, Ryan M.,Caspi, Daniel D.,Trend, Raissa M.,Stoltz, Brian M.
supporting information; experimental part, p. 12978 - 12992 (2010/06/19)
The first palladium-catalyzed enantioselective oxidation of secondary alcohols has been developed, utilizing the readily available diamine (-)-sparteine as a chiral ligand and molecular oxygen as the stoichiometric oxidant. Mechanistic insights regarding the role of the base and hydrogen-bond donors have resulted in several improvements to the original system. Namely, addition of cesium carbonate and tert-butyl alcohol greatly enhances reaction rates, promoting rapid resolutions. The use of chloroform as solvent allows the use of ambient air as the terminal oxidant at 23°C, resulting in enhanced catalyst selectivity. These improved reaction conditions have permitted the successful kinetic resolution of benzylic, allylic, and cyclopropyl secondary alcohols to high enantiomeric excess with good-toexcellent selectivity factors. This catalyst system has also been applied to the desymmetrization of meso-diols, providing high yields of enantioenriched hydroxyketones.
Diastereoselective intermolecular cyclopropanation of simple alkenes by fischer alkenyl and heteroaryl carbene complexes of chromium: Scope and limitations
Barluenga, Jose,Lopez, Salome,Trabanco, Andres A.,Fernandez-Acebes, Alvaro,Florez, Josefa
, p. 8145 - 8154 (2007/10/03)
The intermolecular cyclopropanation of simple alkyl-substituted alkenes with Fischer methoxycarbene complexes under thermal conditions is reported. The scope and limitations of this [2 + 1] cycloaddition with respect to the nature of the carbene complex,
Synthesis of 3-Alkylcatechols via Intramolecular Cyclization
Miyakoshi, Tetsuo,Togashi, Hiroyasu
, p. 407 - 410 (2007/10/02)
The intramolecular cyclization of 2-alkanoyl-2,5-dimethoxytetrahydrofurans 4 with aqueous acid is described. 3-Alkylcatechols 7 were prepared in generally good yields by boiling the dioxane solution of compounds 4 in the presence of 1 M hydrochloric acid.In addition, 4,5-dioxoalkanals 6 were obtained in good to high yields when the dioxane solution of compounds 4 was treated with 0.1 M hydrochloric acid.
Process for producing 2-aceylfuran derivatives
-
, (2008/06/13)
2-Acylfuran derivatives STR1 (R: alkyl, phenyl, etc.; R1 : H, alkyl) are prepared in high yield by reaction, in the presence of a boron trifluoride complex catalyst, of a furan compound STR2 (X: H, Cl, Br; Y: Cl, Br) or with RCOOH in the presence of (XYCHCO)2 O.
DIMETHYLALUMINIUM METHANESELENOLATE - A USEFUL REAGENT FOR THE PREPARATION OF SELENOESTERS. A NEW FRIEDEL-CRAFTS ACYLATION PROCEDURE PROMOTED BY Cu(I)
Kozikowski, Alan P.,Ames, Anthony
, p. 4821 - 4834 (2007/10/02)
The preparation of a new aluminium reagent, dimethylaluminium methaneselenolate (Me2AlSeMe) is described.The reactivity of this aluminium reagent toward a variety of organic substrates has been studied.Me2AlSeMe will convert O-alkyl esters to selenoesters in high yield.These selenoesters function as extremely reactive acyl transfer agents and are converted to acids, esters, and amides on reaction with water, alcohols or amines in the presence of a selenophilic metal cation.The selenoesters will, moreover, acylate reactive arenes and heterocyclic compounds when cuprous triflate is employed as the selenophilic metal cation.This latter transformation constitutes a new transition metal promoted variant of the Friedel-Crafts acylation reaction.
