Biocatalytic Synthesis of Nitrile-Bearing All-Carbon Quaternary Stereocenters.
J Org Chem
; 89(15): 10562-10571, 2024 Aug 02.
Article
em En
| MEDLINE
| ID: mdl-39051740
ABSTRACT
The synthesis of all-carbon quaternary stereocenters containing nitriles is a very important and challenging subject in organic chemistry. We used a biocatalytic approach under mild conditions to obtain new derivatives of these scaffolds by oxidation of catechols by Myceliophthora thermophila laccase (Novozym 51003) to afford o-quinones and 1,4-addition of a series of carbon nucleophiles containing tertiary alkyle nitriles to these intermediates. Using this approach, α-cyano carbonyls bearing a quaternary stereocenter were also prepared. Finally, the yields for the prepared compounds were 72-94%.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2024
Tipo de documento:
Article
País de afiliação:
Irã