Iridium-Catalyzed Asymmetric Hydrogenation of Racemic β-Keto Lactams via Dynamic Kinetic Resolution

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• 作者：Deng-Hui Bao ; Xue-Song Gu ; Jian-Hua XieQi-Lin Zhou
• 刊名：Organic Letters
• 出版年：2017
• 出版时间：January 6, 2017
• 年：2017
• 卷：19
• 期：1
• 页码：118-121
• 全文大小：335K
• ISSN：1523-7052

文摘

A highly efficient Ir-catalyzed asymmetric hydrogenation of racemic β-keto lactams via dynamic kinetic resolution (DKR) for the synthesis of optically active β-hydroxyl lactams has been described. With the Ir-SpiroSAP catalyst, a series of racemic β-keto lactams including β-keto γ-, δ-, and ε-lactams were hydrogenated to chiral β-hydroxy lactams in high yields (87–99%) with excellent enantio- and diastereoselectivity (83–99.9% ee, syn/anti: 97:3–>99:1) at low catalyst loading under mild reaction conditions. This efficient method has been successfully applied in the synthesis of the chiral intermediate of fluoroquinolone antibiotic premafloxacine.