16195-87-2Relevant articles and documents
Chemoselective Biohydrogenation of Alkenes in the Presence of Alkynes for the Homologation of 2-Alkynals/3-Alkyn-2-ones into 4-Alkynals/Alkynols
Colombo, Danilo,Brenna, Elisabetta,Gatti, Francesco G.,Ghezzi, Maria Chiara,Monti, Daniela,Parmeggiani, Fabio,Tentori, Francesca
supporting information, p. 2638 - 2648 (2019/05/16)
The chemoselective hydrogenation of alkenes in the presence of alkynes is a very challenging transformation to achieve with traditional chemical methods. The development of an effective procedure to perform this transformation would enrich the tool-kit available to organic chemists for the development of useful synthetic routes, and the creation of novel structural motifs. The reduction of activated alkene bonds by ene-reductases (ERs) is completely chemoselective, because of the mechanism of the reaction. Thus, we investigated the use of ERs belonging to the Old Yellow Enzyme family for the reduction of α,β-unsaturated aldehydes with a conjugated C≡C triple bond at the γ position. This reaction was exploited as the key step for the development of an effective homologation route to convert aryl and alkyl substituted propynals and butynones into 4-alkynals and 4-alkynols, avoiding some troublesome or hazardous steps of known synthetic routes. (Figure presented.).
Weakly ligated palladium complexes PdCl2(RCN)2 in piperidine: Versatile catalysts for Sonogashira reaction of vinyl chlorides at room temperature
Alami, Mouad,Crousse, Benoit,Ferri, Fabiola
, p. 114 - 123 (2007/10/03)
Copper iodide and weakly ligated palladium complexes PdCl2(RCN)2 (R = Ph, Me) catalyzed efficiently the coupling reaction of vinyl chlorides with 1-alkynes in the presence of piperidine to give the corresponding conjugated enynes in good to excellent yields. The reaction takes place rapidly and cleanly at room temperature. Application to the synthesis of terbinafine which exhibits strong antimycotic activity has been realized.
A PRACTICAL SYNTHESIS OF (2E,6E,8E)-N-(2-METHYLPROPYL)-2,6,8-HEXADECATRIEN-10-YNAMIDE
Sharma, G. V. M.,Rajagopal, D.,Sreenivasa Rao, E.
, p. 3181 - 3190 (2007/10/02)
A convergent and practical synthesis of (2E,6E,8E)-N-(2-methylpropyl)-2,6,8-hexadecatrien-10-ynamide is described.
