- Dynamic Kinetic Asymmetric Reductive Amination: Synthesis of Chiral Primary β-Amino Lactams
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A highly efficient ruthenium-catalyzed asymmetric reductive amination (ARA) of racemic β-keto lactams with molecular hydrogen and ammonium salts is disclosed for the synthesis of enantiomerically pure primary amino lactams through dynamic kinetic resolution (DKR). By this approach, a range of syn primary β-amino lactams were obtained in high yields with high chemo-, enantio-, and diastereoselectivity (up to 98 % yield, 99 % ee, >20:1 d.r., syn products). The utility of the products has been demonstrated by rapid access to a key synthetic intermediate towards biologically active drug molecules. Meanwhile, mechanistic studies and control experiments indicate that the reaction may proceed through the hydrogenation of an iminium intermediate.
- Lou, Yazhou,Hu, Yutao,Lu, Jiaxiang,Guan, Fanfu,Gong, Gelin,Yin, Qin,Zhang, Xumu
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supporting information
p. 14193 - 14197
(2018/10/15)
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- Facile Synthesis of Spirocyclic Lactams from β-Keto Carboxylic Acids
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A facile synthesis of spirocyclic lactams starting from β-keto carboxylic acids via a one-pot cascade reaction involving a Curtius rearrangement and an intramolecular nucleophilic addition of the enol carbon to the isocyanate intermediate is reported. The same conditions have also been used for the generation of fused cyclic lactams with similar good yields. The synthetic value of this method has been demonstrated by efficient synthesis of tetracyclic spirolactam 8 and pentacyclic spirolactam 9.
- Yang, Wei,Sun, Xianyu,Yu, Wenbo,Rai, Rachita,Deschamps, Jeffrey R.,Mitchell, Lauren A.,Jiang, Chao,Mackerell, Alexander D.,Xue, Fengtian
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supporting information
p. 3070 - 3073
(2015/06/30)
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