14274-30-7Relevant articles and documents
Synthetic strategy toward γ-KETO NITRILES and their Biocatalytic conversion to asymmetric γ-lactones
Franz, Sarah E.,Watkins, Richard R.,Wright, Laura A.,Weaver, Blair A.,Hartage, Ramon C.,Ghiviriga, Ion,Gumina, Giuseppe,Feske, Brent D.
, p. 2171 - 2178 (2013/08/23)
Asymmetric γ-hydroxy nitriles are valuable intermediates because hydrolysis of the nitriles can result in an intramolecular cyclization to chiral γ-lactones, which have a variety of biological uses. Starting with an assortment of different aldehydes (alkyl and aryl) a 4-step synthesis of γ-keto nitriles was developed. These prochiral substrates were then screened against a library of ketoreductases for their ability to stereoselectively reduce the carbonyl. Enzymes from the short chain dehydrogenase family showed activity and these enzymatic reactions were scaled up to produce a diverse set of chiral γ-lactones.
A mild and efficient Nef reaction for the conversion of nitro to carbonyl group by dimethyldioxirane (DMD) oxidation of nitronate anions
Adam, Waldemar,Makosza, Mieczyslaw,Saha-M?ller, Chantu R.,Zhao, Cong-Gui
, p. 1335 - 1336 (2007/10/03)
DMD oxidation of nitronate onions, generated in situ from the corresponding nitroalkanes, affords the corresponding carbonyl products. Highest yields were obtained when one equivalent of water was added before the oxidation with DMD.
Acylcobalt Salophen Reagents. Precursors to Acyl Radical Intermediates for Use in Carbon-to-Carbon Bond-forming Reactions to Alkenes
Coveney, Donal J.,Patel, Vinod F.,Pattenden, Gerald,Thompson, David M.
, p. 2721 - 2729 (2007/10/02)
Acylcobalt salophen reagents (6) are conveniently synthesised from carboxylic acid chlorides following treatment with the sodium derivative (5) produced from reduction of cobalt(II) salophen with sodium amalgam in tetrahydrofuran at room temperature.The acylcobalt salophens (6) undergo homolytic cleavage in the presence of light from a conventional 300 W sunlamp to give acyl radicals (24) which then undergo additions to activated carbon-to-carbon double bonds, leading to enones, viz. (26) , or saturated ketones, viz. (34) .Intramolecular cyclisations of the acylcobalt salophens (42a) and (42b) lead to the ylidenecyclopentanones (43) and (45), respectively.