91344-52-4Relevant academic research and scientific papers
Enantioselectivity of some 1-(benzofuran-2-yl)-1-(1-H-imidazol-1-yl) alkanes as inhibitors of P450(Arom)
Khodarahmi, G. Ali,Smith, H. John,Nicholls, Paul J.,Ahmadi, Masoud
, p. 1321 - 1330 (2007/10/03)
The low stereospecificity of the enantiomers of 1-[(benzofuran-2-yl)-4-chlorophenylmethyl]imidazole (6, R = H, R' = 4'-Cl) and the corresponding 4-fluoro compound as inhibitors of aromatase (P450(Arom)) has been explored using 1-(5,7-dichlorobenzofuran-2-yl)-1-(1H-imidaz-1-yl)ethane (7, R1 = R2 = Cl, R = CH3), -propane (7, R1 = R2 = Cl, R = C2H5), and the corresponding 5,7-dibromo compounds resolved as their dibenzoyl-D (or -L) tartrates. Low enantioselectivity ratios of 4.8 (5,7-diCl) and 12.6 (5,7-diBr) were shown for the ethanes. The values for the corresponding propanes were 8.3 and 5.2, respectively, and for these compounds the stereoselectivity was reversed.
Stereoselective Reduction of γ-Oxobutanoic Acids Using DIBAL-H and ZnCl2
Frenette, R.,Monette, M.,Bernstein, M. A.,Young, R. N.,Verhoeven, T. R.
, p. 3083 - 3089 (2007/10/02)
A variety of γ-aromatic γ-ketobutanoic acids can be reduced selectively, under optimized conditions, by the use of DIBAL-H and ZnCl2 to provide the (RS,SR)-γ-aryl-γ-hydroxy-β-methylbutanoic acids.Further evidence has been gathered to support the hypothesis that the reaction proceeds by formation of a seven-membered ring complex with the aluminium or zinc atom bridging the ketone and carboxyl groups which preceeds the reduction step and that this templated reduction accounts for observed high diastereoselectivity.Also we have shown that some γ-aryl-γ-butyrolactones can be easily transformed via an oxidative cleavage of the aromatic ring to provide selective synthesis of either cis- or trans-tetrahydro-3-methyl-5-oxo-2-furancarboxylic acid derivatives.
AN EFFICIENT FRIEDEL-CRAFTS SYNTHESIS OF 2-ACYLBENZOFURANS
Gill, Melvyn
, p. 621 - 626 (2007/10/02)
2-(Trimethylsilyl)benzofuran, available quantitatively from benzofuran itself, reacts rapidly with primary, secondary, and tertiary aliphatic carboxylic acid chlorides in the presence of titanium(IV) chloride at low temperature to afford the corresponding 2-acylbenzofurans in excellent yields.This approach offers significant synthetic advantage over existing routes to the title compounds.
