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

作者：Zhang, Haowei; Yang, Bing; Yang, Zhen; Lu, Hongjian; Li, Guigen^*

来源：Journal of Organic Chemistry, 2016, 81(17): 7654-7661.

DOI：10.1021/acs.joc.6b01385

• ALPHA-AMINO-ACIDS
• MICHAEL ADDITION-REACTIONS
• AZA-HENRY REACTION
• GAP CHEMISTRY
• NUCLEOPHILIC GLYCINE
• PYROGLUTAMIC ACIDS
• NI(II) COMPLEXES
• DESIGN
• STEREOSELECTIVITY
• HOMOLOGATION

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 alpha-methyl-alpha,beta-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.

• 出版日期2016-9-2
• 单位南京大学