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Kim, Heebum; Kim, Yeongju; Kim, Sung‐Gon
Advanced synthesis & catalysis, April 23, 2024, Letnik: 366, Številka: 8Journal Article
Dihydroquinolin‐2‐ones, recognized for their bioactive properties, feature a six‐membered structure with nitrogen‐containing heterocycles. A method has been developed for synthesizing enantioenriched 3,4‐dihydroquinoline‐2‐one derivatives. This approach utilizes an asymmetric 4+2‐cyclization process, combining 2‐amino‐β‐nitrostyrenes with azlactones, and is facilitated by a bifunctional squaramide‐based organocatalyst. This process has enabled the creation of chiral 3,4‐dihydroquinoline‐2‐ones with complex structures, including chiral tetrasubstituted carbon stereocenters, delivering corresponding products in 26–95% yield with a diastereomeric ratio of 1.2:1–19:1 and 52–97 ee.
