BioChem - DOS

Chemoselective Biohydrogenation of Alkenes in the Presence of Alkynes for the Homologation of 2-Alkynals/3-Alkyn-2-ones into 4-Alkynals/Alkynols

Advanced synthesis & catalysis

Colombo, Danilo; Brenna, Elisabetta; Gatti, Francesco G.; Ghezzi, Maria Chiara; Monti, Daniela; Parmeggiani, Fabio; Tentori, Francesca

<P><B>Abstract</B></P><P>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&#8208;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&#8208;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 &alpha;,&beta;&#8208;unsaturated aldehydes with a conjugated C&equiv;C triple bond at the &gamma; 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&#8208;alkynals and 4&#8208;alkynols, avoiding some troublesome or hazardous steps of known synthetic routes.</P>

2019

1615-4150

1615-4169

361

11

pp.2638-2648

10.1002/adsc.201900177

http://click.ndsl.kr/servlet/OpenAPIDetailView?keyValue=05787966&target=NART&cn=NART97255672

alkynes; biocatalysis; green chemistry; oxidoreductases; bioreduction