Rezaei Elaheh, Shahedi Mansour, Habibi Zohreh
Department of Organic Chemistry, Shahid Beheshti University, 1983969411 Tehran, Iran.
J Org Chem. 2024 Aug 2;89(15):10562-10571. doi: 10.1021/acs.joc.4c00793. Epub 2024 Jul 25.
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 laccase (Novozym 51003) to afford -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%.
含有腈基的全碳季碳立体中心的合成是有机化学中一个非常重要且具有挑战性的课题。我们采用生物催化方法，在温和条件下通过漆酶（诺维信51003）氧化儿茶酚得到对醌，并使一系列含有叔烷基腈的碳亲核试剂与这些中间体进行1,4-加成反应，从而获得这些骨架的新衍生物。利用该方法，还制备了带有季碳立体中心的α-氰基羰基化合物。最后，所制备化合物的产率为72% - 94%。
