Turek-Herman Joshua R, Rosenberger Mike, Hyster Todd K
Department of Chemistry and Chemical Biology, Cornell University, Ithaca, NY 14853, USA.
Asian J Org Chem. 2023 Aug;12(8). doi: 10.1002/ajoc.202300274. Epub 2023 Jul 7.
Quaternary carbons are useful motifs in chemical synthesis but can be challenging to prepare using many chemical methods. Here, we report a stereoselective synthesis of -quaternary lactams using flavin-dependent 'ene'-reductases via a 5-exo-trig radical cyclization. The products are formed in moderate to good levels of enantioselectivity using an 'ene'-reductase variant from . This method highlights the opportunity for biocatalysis to form quaternary centers using non-natural reactions.
季碳在化学合成中是有用的结构单元，但使用许多化学方法制备时可能具有挑战性。在此，我们报道了通过黄素依赖性“烯”还原酶，经由5-外向-三自由基环化反应立体选择性合成γ-季碳内酰胺。使用来自[具体来源]的“烯”还原酶变体，产物以中等至良好的对映选择性水平形成。该方法突出了生物催化利用非天然反应形成季碳中心的机会。
