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Jhang, Yin-Jia; Zhelavskyi, Oleksii; Nagorny, Pavel
Organic letters, 10/2023, Letnik: 25, Številka: 42Journal Article
This article describes the asymmetric synthesis of chiral aziridinoquinoxalines using (R)-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 (R)-configuration of the newly formed stereocenter (32–61% yield and 64–99% ee for the (R,R,R)-diastereomers and 7–46% yield and 97–99% ee for the (S,S,R)-diastereomers). This process could be coupled to ring-opening of the (S,S,R)-diastereomer with thiophenol to produce chiral tetrahydroquinoxalines with three contiguous stereocenters.
