123707-41-5Relevant academic research and scientific papers
Substrate scope and synthetic applications of the enantioselective reduction of α-alkyl-β-arylenones mediated by Old Yellow Enzymes
Brenna, Elisabetta,Cosi, Sara Lucia,Ferrandi, Erica Elisa,Gatti, Francesco G.,Monti, Daniela,Parmeggiani, Fabio,Sacchetti, Alessandro
supporting information, p. 2988 - 2996 (2013/07/25)
The ene-reductases mediated bioreduction of a selection of open-chain α-alkyl-β-aryl enones afforded the corresponding saturated α-chiral ketones in high yield and optical purity in several cases. The stereo-electronic requirements of the reaction have been investigated, considering the nature and location of substituents on the aromatic ring as well as the steric hindrance at the α-position and adjacent to the carbonyl functionality. The general considerations drawn allow us to guide the design of α,β-unsaturated ketones to be employed as substrates of ene-reductases in future preparative applications. An interesting case of orthogonality between enzyme-based and substrate-based stereocontrol within the highly homologous ene-reductases from Saccharomyces species (OYE1-3) has been reported and rationalized with the help of computational docking studies. Furthermore, to demonstrate the synthetic versatility of the reaction, the key chiral precursors of biologically active compounds such as (2′R)- stenusines and (S)-iopanoic acid were obtained. The very robust protocol allowed us to run the reactions on preparative scale in quantitative yields, with a simple work-up and no chromatographic purification steps. The Royal Society of Chemistry 2013.
Highly stereoselective facile synthesisl of 2-acetoxy-1,3(E)-alkadienes via a Rh(I)-catalyzed isomerization of 2,3- allenyl carboxylates
Zhang, Xiaobing,Fu, Chunling,Ma, Shengming
, p. 1920 - 1923 (2011/06/21)
A highly stereoselective Rh(I)-catalyzed 1,3-acetoxyl rearrangement of 1,2-allen-3-yl carboxylates leading to 2-acetoxy-1,3(E)-alkadienes has been developed. In addition to the high catalytic efficiency and the scope, the excellent E-selectivity of the do
Organic Compounds
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Page/Page column 8, (2010/05/13)
Disclosed are compounds having the ability to inhibit cytochrome P450 2A6, 2A13, and/or 2B6 and tobacco products comprising them. Also disclosed are pharmaceutical compositions comprising them.
ORGANIC COMPOUNDS
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Page/Page column 28, (2008/12/04)
Disclosed are compounds having the ability to modulate, namely to improve, enhance and or modify fragrance compositions due to their ability to inhibit cytochrome P450 enzymes, e.g. CYP2A13 and CYP2B6.
Sequential Reactions of Michael Addition and Peterson Condensation of 1-Silylvinyl Ketones with Grignard Reagents: Study of Stereoselectivity
Tanaka, Junji,Kobayashi, Hiroshi,Kanemasa, Shuji,Tsuge, Otohiko
, p. 1193 - 1197 (2007/10/02)
1-Silylvinyl ketones undergo smooth Michael addition with Grignard reagents generating magnesium enolates which are then trapped with benzaldehyde to give E- and Z-isomers of enones after Peterson condensation. (E)-Olefins become major products under a thermodynamic control when the condensation with benzaldehyde is carried out at room temperature in diethyl ether, while Z-isomers are more favored as kinetically controlled products at -78 deg C in THF.Reaction mechanism is briefly discussed.
