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- Title
Asymmetric C-C Bond Formation between Chiral N-Phosphonyl Imines and a Nickel(II)-Complexed Glycine Schiff Base Provides Efficient Synthesis of α,β- syn-Diamino Acid Derivatives.
- Authors
Sun, Hao; Zhang, Haowei; Han, Jianlin; Pan, Yi; Li, Guigen
- Abstract
The group-assisted purification asymmetric synthesis of α,β-diamino acid derivatives was achieved by treating chiral N-phosphonyl imines with a NiII-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 (>30:1 dr) and high yields (91-97 %). The absolute stereochemistry was unambiguously determined by X-ray structure analysis.
- Subjects
CHEMICAL bonds; GLYCINE; DIAMINO amino acids; SCHIFF base derivatives; X-ray crystallography; STEREOCHEMISTRY
- Publication
European Journal of Organic Chemistry, 2013, Vol 2013, Issue 22, p4744
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201300554