Jhang Yin-Jia, Zhelavskyi Oleksii, Nagorny Pavel
Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, United States.
Org Lett. 2023 Oct 27;25(42):7721-7726. doi: 10.1021/acs.orglett.3c03072. Epub 2023 Oct 18.
This article describes the asymmetric synthesis of chiral aziridinoquinoxalines using ()-TRIP-catalyzed parallel kinetic resolution under transfer hydrogenation conditions. This resolution was successfully accomplished for 16 different substrates and led to highly enantioenriched diastereomers with the ()-configuration of the newly formed stereocenter (32-61% yield and 64-99% ee for the ()-diastereomers and 7-46% yield and 97-99% ee for the ()-diastereomers). This process could be coupled to ring-opening of the ()-diastereomer with thiophenol to produce chiral tetrahydroquinoxalines with three contiguous stereocenters.
本文描述了在手性转移氢化条件下，使用()-TRIP催化的平行动力学拆分法对手性氮杂环丙烷并喹喔啉进行不对称合成。该拆分法成功应用于16种不同的底物，得到了新形成的立体中心具有()-构型的高度对映体富集的非对映异构体（()-非对映异构体的产率为32 - 61%，对映体过量值为64 - 99%；()-非对映异构体的产率为7 - 46%，对映体过量值为97 - 99%）。该过程可与()-非对映异构体与苯硫酚的开环反应相结合，以生成具有三个相邻立体中心的手性四氢喹喔啉。
