- Organo-catalyzed Michael addition of 2-fluoro-2-arylacetonitriles
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An efficient synthesis of a variety of 2-arylacetonitriles containing a fluorinated stereogenic center through organo-catalyzed Michael addition reaction of 2-fluoro-2-arylacetonitriles has been developed. This protocol uses a cheap organocatalyst (DBU) and has a broad substrate scope: α, β-unsaturated ketones, esters, nitriles and sulfones were all successfully reacted. Importantly, water proved to be a good solvent for this reaction.
- Chen, De-Yin,Song, Shuai,Chen, Ling-Yan,Ren, Xinfeng,Li, Ya
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supporting information
(2021/03/01)
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- One-pot access to 2-amino-3-arylbenzofurans: Direct entry to polyheterocyclic chemical space
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As a means to make new benzofuran-embedded polycyclic structures, we established two efficient one-pot sequential coupling routes to 2-amino-3-arylbenzofurans and 2-amino-3-arylnaphtho[2,1-b]furans. Further ring formation (six- and seven-membered rings) with the resulting amine moiety at the C2 position of benzofurans was realized, leading to further expansion of benzofuran-based chemical space.
- Joshi, Dirgha Raj,Kim, Ikyon,Lee, Jeong Hwa,Prasad, Sure Siva
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p. 8119 - 8140
(2020/11/03)
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- Nanoceria as a recyclable catalyst/support for the cyanosilylation of ketones and alcohol oxidation in cascade
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The cyanosilylation of carbonyl compounds is a fundamental reaction in organic synthesis, to give cyanohydrins. Ketones are particularly reluctant to cyanosilane addition and require the action of a catalyst, and despite many soluble Br?nsted and Lewis ac
- Garnes-Portolés, Francisco,Leyva-Pérez, Antonio,Rivero-Crespo, Miguel ángel
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- Solvent-free cyanosilylation of aromatic and heteroaryl aldehydes catalyzed by a cationic iron N-heterocyclic carbene complex at ambient temperature under UV irradiation
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The cyanosilylation of aromatic aldehydes and heteroaryl aldehydes with trimethylsilyl cyanide (TMSCN) is efficiently catalyzed by an iron complex of the type {[3-isopropyl-1-(1R-phenylethyl)imidazol-2-ylidene]Fe(CO)2}I (3) in presence of UV li
- Kumar, Dharmendra,Prakasham,Gangwar, Manoj Kumar,Ghosh, Prasenjit
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supporting information
(2019/08/07)
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- Lewis Acid Mediated Nazarov Cyclization as a Convergent and Enantioselective Entry to C-nor-D-homo-Steroids
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A straightforward synthesis of C-nor-D-homo steroids starting from (+)-Wieland–Miescher ketone is reported. This convergent synthetic strategy utilizes a?scalable diastereoselective Nazarov cyclization of functionalized chiral aryl vinyl ketones, allowing for further functionalization. The ability to conduct this key transformation on a multi-gram scale paves the way for the synthesis of a variety of completely new C-nor-D-homo steroids, without the need of a classic steran steroid rearrangement or achiral linear reaction sequences.
- Krieger, Johannes,Smeilus, Toni,Schackow, Oliver,Giannis, Athanassios
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supporting information
p. 5000 - 5004
(2017/04/18)
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- Applications of Optically Active Aryl Cyanohydrins in the Synthesis of α-Hydroxy Aldehydes, α-Hydroxy Ketones and β-Hydroxy Amines
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Cyanohydrins, prepared in high optical purity from aryl aldehydes, have been converted into α-hydroxy aldehydes, α-hydroxy ketones and β-hydroxy amines without any racemization and frequently with good stereoselectivity for the erythro-diastereoisomer (>90percent) at the newly introduced stereogenic centre.
- Jackson, W. Roy,Jacobs, Howard A.,Jayatilake, Gamini S.,Matthews, Barry R.,Watson, Keith G.
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p. 2045 - 2062
(2007/10/02)
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- Enzymatic Preparation of Optically Active Cyanohydrin Acetates
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A series of cyanohydrin acetates (1)-(47) of widely varying structures, potential chiral building blocks for numerous synthetic applications, has been prepared in good chemical and often high optical yields by enzymatic hydrolysis of their racemic acetates in the presence of an ester hydrolase from Pseudomonas sp.
- Almsick, Andreas van,Buddrus, Joachim,Hoenicke-Schmidt, Petra,Laumen, Kurt,Schneider, Manfred P.
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p. 1391 - 1393
(2007/10/02)
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- Specific dopamine D-1 and DA1 properties of 4-(mono- and -dihydroxyphenyl)-1,2,3,4-tetrahydroisoquinoline and its tetrahydrothieno[2,3-c]pyridine analogue
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The title compounds were prepared and examined to elucidate further the structure-activity relationships of dopamine agonists related to nomifensine. Two of the compounds, 4-(3,4-dihydroxyphenyl)-1,2,3,4-tetrahydroisoquinoline and 4-(3,4-dihydroxyphenyl)-
- Riggs,Nichols,Foreman,Truex,Glock,Kohli
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p. 1454 - 1458
(2007/10/02)
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- A NOVEL SYNTHESIS OF α-FLUOROOACETONITRILES. APPLICATION TO A CONVENIENT PREPARATION OF 2-FLUORO-2-PHENETYLAMINES
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α-Fluorophenylacetonitriles (3) are readily prepared by the treatment of the corresponding benzaldehyde cyanohydrin trimethylsilylethers (2) with diethylaminosulfur trifluoride (DAST).This method for the introduction of fluorine alpha to the cyano group is also applicable to the cyanohydrin trimethylsilylethers of aromatic ketones.Diborane reduction of the α-fluorophenylacetonitriles (3) yields 2-fluoro-2-phenethylamines (4).
- LeTourneau, Michael E.,McCarthy, James R.
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p. 5227 - 5230
(2007/10/02)
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- 1-(4-Aminobenzyl)- and 1-(4-aminophenyl)isoquinoline derivatives: Synthesis and evaluation as potential irreversible cyclic nucleotide phosphodiesterase inhibitors
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In an effort to increase the specificity of the potent phosphodiesterase inhibitor papaverine, we synthesized two series of novel 1-(4-aminobenzyl)- and 1-(4-aminophenyl)isoquinoline derivatives, incorporating alkylating moieties on the amine substituents. These compounds were evaluated for their inhibitory action on phosphodiesterase preparations from bovine heart and rat cerebral cortex. Studies were also conducted to determine whether these compounds were reacting with the enzymes in an irreversible manner. The compounds were potent inhibitors of the phosphodiesterases; however, no evidence was found for an irreversible inhibition.
- Walker,Boots,Stubbins,Rogers,Davis
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p. 174 - 181
(2007/10/02)
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