81156-45-8Relevant academic research and scientific papers
PREPARATION OF 4-HYDROXY-2-ALKENENITRILES FROM PHENYLSULFINYLACETONITRILE WITH KETONES OR ALDEHYDES, AND ITS SYNTHETIC APPLICATION TO SUBSTITUTED FURANS
Nokami, J.,Mandai, T.,Imakura, Y.,Nishiuchi, K.,Kawada, M.,Wakabayashi, S.
, p. 4489 - 4490 (1981)
The reaction of phenylsulfinylacetonitrile 1 with ketones or aldehydes gave 4-hydroxy-2-alkenenitrils which were converted to 2- and/or 3-substituted furans by the treatment with diisobutylaluminiumhydride(DIBAL) followed by acid hydrolysis.
Convenient procedure of Horner-Wadsworth-Emmons olefination for the synthesis of simple and functionalized α,β-unsaturated nitriles
Lattanzi, Alessandra,Orelli, Liliana R.,Barone, Patrizia,Massa, Antonio,Iannece, Patrizia,Scettri, Arrigo
, p. 1333 - 1337 (2007/10/03)
A mild and practical procedure of Horner-Wadsworth-Emmons olefination promoted by lithium hydroxide and α-cyano phosphonates has been set up for the synthesis of α,β-unsaturated nitriles. The reaction conditions are tolerated by functionalized ketones and the exclusive formation of E-γ-hydroxy α,β-unsaturated nitriles has been observed.
Biotransformation of αβ-unsaturated carbonyl compounds: sulfides, sulfoxides, sulfones, nitriles and esters by yeast species: carbonyl group and carbon-carbon double bond reduction
Koul, Surinder,Crout, David H. G.,Errington, William,Tax, Jiri
, p. 2969 - 2988 (2007/10/03)
The reduction of αβ-unsaturated ketones with γ-sulfide, sulfoxide, sulfone, nitrile and ester functions has been investigated.Both C=O and C=C reduction was observed.In the sulfur series, C=O bond reduction was always observed, but significant C=C bond reduction was observed only with the sulfide.The unsaturated nitriles gave the corresponding alcohols as the major bioreduction product, with smaller but significant amounts of fully reduced product.A similar result was obtained with the ester substrate.Relative and absolute configurations of bioreduction products were determined.A comparison was made between reductions catalysed by bakers' yeast (Saccharomyces cerevisiae) and by other yeasts (Zygosaccharomyces rouxii, Pichia capsulata, P. farinosa, Candida chalmersi and C. diddensiae).The tendency of Z. rouxii to give products enantiomeric with thouse obtained using S. cerevisiae was noted.The relationship between substrate structure and the stereochemistry of C=C double bond reduction is discussed.
