Asymmetric Synthesis of Chiral α-Methyl-α,β-diamino Acid Derivatives via Group-Assisted Purification Chemistry Using N-Phosphonyl Imines and a Ni(II)-Complexed Alanine Schiff Base

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• 作者：Haowei Zhang ; Bing Yang ; Zhen Yang ; Hongjian Lu ; Guigen Li
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：September 2, 2016
• 年：2016
• 卷：81
• 期：17
• 页码：7654-7661
• 全文大小：447K
• 年卷期：0
• ISSN：1520-6904

文摘

The Mannich reaction between chiral N-phosphonyl imines and a Ni(II)-complexed alanine Schiff base (Ala-Ni) is reported. With a chiral phosphonyl auxiliary, a single isomer of α-methyl-α,β-diamino acid derivative containing vicinal chiral centers, including a chiral quaternary carbon center, can be obtained simply by washing the crude mixture with cosolvents. The absolute stereochemistry of the enantiomerically pure product has been unambiguously determined by X-ray crystallographic analysis.