Asymmetric C-C Bond Formation between Chiral N-Phosphonyl Imines and a Nickel(II)-Complexed Glycine Schiff Base Provides Efficient Synthesis of alpha,beta-syn-Diamino Acid Derivatives

作者：Sun Hao; Zhang Haowei; Han Jianlin; Pan Yi^*; Li Guigen

来源：European Journal of Organic Chemistry, 2013, 2013(22): 4744-4747.

DOI：10.1002/ejoc.201300554

• Asymmetric synthesis
• Amino acids
• Schiff bases
• Nickel
• Phosphorus

The group-assisted purification asymmetric synthesis of alpha,beta-diamino acid derivatives was achieved by treating chiral N-phosphonyl imines with a Ni-II-complexed glycine-derived enolate; traditional purification techniques such as chromatography and recrystallization are not required. Successful control of the syn stereochemistry of the vicinal diamino products complements our previous methods that afforded anti stereoisomers; thus, all four individual isomers can be synthesized simply by changing the geometry of the enolate. In contrast to our previous synthesis in which at least 5 equiv. of the glycine Schiff base enolate was required for complete conversion, the new synthesis only needs 1.1 equiv. of the glycine Schiff base enolate to give complete diastereoselectivity (%26gt;30:1dr) and high yields (91-97%). The absolute stereochemistry was unambiguously determined by X-ray structure analysis.

• 出版日期2013-8
• 单位南京大学