51765-78-7

Upstream product

• 17851-98-8 1-phenyl-1-(tributylstannyloxy)ethene 
• 19481-82-4 2-bromopropionitrile 
• 1617-17-0 2-chlorpropionitrile 
• 66324-10-5 tert-butyldimethyl(1-phenylvinyloxy)silane 
• 591-51-5 phenyllithium 
• 52755-38-1 1-phenyl-2-buten-1-ol 
• 35660-91-4 (E)-1-phenyl-2-buten-1-one 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 100-52-7 benzaldehyde 
• 80735-94-0 1-Phenyl-3-buten-1-ol 
• 6249-80-5 1-phenylbut-3-en-1-one 
• 7677-24-9 trimethylsilyl cyanide 
• 495-41-0 1-phenylbut-2-en-1-one 

Relevant academic research and scientific papers

A Photochemical Organocatalytic Strategy for the α-Alkylation of Ketones by using Radicals

Reported herein is a visible-light-mediated radical approach to the α-alkylation of ketones. This method exploits the ability of a nucleophilic organocatalyst to generate radicals upon SN2-based activation of alkyl halides and blue light irradiation. The resulting open-shell intermediates are then intercepted by weakly nucleophilic silyl enol ethers, which would be unable to directly attack the alkyl halides through a traditional two-electron path. The mild reaction conditions allowed functionalization of the α position of ketones with functional groups that are not compatible with classical anionic strategies. In addition, the redox-neutral nature of this process makes it compatible with a cinchona-based primary amine catalyst, which was used to develop a rare example of enantioselective organocatalytic radical α-alkylation of ketones.

Structural study-guided development of versatile phase-transfer catalysts for asymmetric conjugate additions of cyanide

Unprecedented phase-transfer catalysts for the first example of an organocatalytic asymmetric conjugate addition of cyanide with acetone cyanohydrin are reported (see scheme). Utilizing an accessible cupreidinium salt and a cyanation reagent suitable for industrial scale, this reaction holds significant promise for practical asymmetric synthesis. The catalysts were developed as a result of key structural insights gained by X-ray analysis. Copyright

Asymmetric hydrocyanation of α,β-unsaturated ketones into β-cyano ketones with the [Ru(phgly)2(binap)]/C6H 5OLi catalyst system

Enantioselective conjugate addition of HCN to α,β-unsaturated ketones catalyzed by the combined system of [Ru{(S)-phgly}2{(S)- binap}] and C6H5OLi has afforded β-cyano ketones in high yield (see scheme). No detectable amount of the corresponding 1,2-adduct was produced and tert-C4H9OCH3 was the solvent of choice. The cyanation was conducted with a substrate-to-catalyst molar ratio in the range of 200:1-1000:1 at -20-0°C. Copyright

Highly efficient Cs2CO3-catalyzed 1,4-addition of Me3SiCN to enones with water as the additive

A facile and efficient 1,4-addition of Me3SiCN to enones has been achieved with perfect regioselectivity using Cs2CO3 as catalyst. Thus, with 0.5 mol% of Cs2CO3 and 4 equivalents of H2O as the additive excellent yields (81-99%) of -cyanoketones are obtained within one to five hours. Both aromatic and aliphatic enones are found suitable substrates for this protocol. Georg Thieme Verlag Stuttgart · New York.

Highly efficient syntheses of β-cyanoketones via conjugate addition of Me3SiCN to aromatic enones

An efficient 1,4-addition of Me3SiCN to aromatic enones has been achieved with excellent yields (91%-99%) using CsF (1 mol%) as the catalyst and H2O (4 equiv.) as the additive in refluxing dioxane within 7 h. The perfect regioselecti

The highly efficient 1,4-addition of TMSCN to aromatic enones catalyzed by CsF with water as the additive

An efficient 1,4-addition of TMSCN to aromatic enones has been achieved in excellent yields (91-99%) by CsF (1 mol%) as the catalyst and H2O (4 equiv) as the additive in refluxing dioxane within 2-7 hours. Georg Thieme Verlag Stuttgart - New Yo

Synthetic utility of stannyl enolates as radical alkylating agents

(Equation presented) The radical-initiated β-ketoalkylation of haloalkanes with tributylstannyl enolates is described. Stannyl enolates derived from aromatic ketones are reactive toward the homolytic β-ketoalkylation of simple haloalkanes as well as those activated by an electron-withdrawing group. The reactivity of stannyl enolates as radical alkylating agents can be utilized for an efficient three-component coupling reaction among stannyl enolates, haloalkanes, and electron-deficient alkenes.

SUBSTITUTED THIO-SUBSTITUTED BENZYL-PROPIONYL-L-PROLINES

This disclosure describes novel substituted ω-aroyl(propionyl or butyryl)-L-prolines and the esters and cationic salts thereof which are useful as hypotensive agents in mammals.

Process for preparing ketones

Ketones are prepared by reacting an aromatic or heterocyclic aldehyde in the presence of a cyanide ion with an unsaturated compound having the formula (I): STR1 wherein R1, R2 and R3 are the same or different and are selected from the group of hydrogen, optionally substituted aliphatic, cycloaliphatic, araliphatic, aromatic, heterocyclic and carboxylic acid ester and R4 is nitrile (CN), --CO--R5 or --CO--OR5 wherein R5 is selected from the group of optionally substituted aliphatic, cycloaliphatic, araliphatic, aromatic and heterocyclic and R1 and R2 and/or R1 and R3 and/or R2 and R5 or R3 and R5 together with the carbon atoms to which they are attached as substituents may also form a carbocyclic or heterocyclic ring. Ketones prepared according to the process of the invention have the formula: STR2 wherein R1 ' and R3 ' are identical or different and are selected from the group of hydrogen, lower alkyl having up to 3 C-atoms and optionally substituted phenyl; and R6 ' is optionally substituted phenyl or a pyridyl.