850341-44-5Relevant academic research and scientific papers
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
, 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.).
Total syntheses of amphidinolides T1 and T4 via catalytic, stereoselective, reductive macrocyclizations
Colby, Elizabeth A.,O'Brien, Karen C.,Jamison, Timothy F.
, p. 4297 - 4307 (2007/10/03)
Described in this work are total syntheses of amphidinolides T1 and T4 using two nickel-catalyzed reductive coupling reactions of alkynes, with an epoxide in one case (intermolecular) and with an aldehyde in another (intramolecular). The latter was used t
