Abstract
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.
| Original language | English |
|---|---|
| Pages (from-to) | 7654-7661 |
| Number of pages | 8 |
| Journal | Journal of Organic Chemistry |
| Volume | 81 |
| Issue number | 17 |
| DOIs | |
| State | Published - Sep 2 2016 |
Fingerprint Dive into the research topics of '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'. Together they form a unique fingerprint.
Cite this
Zhang, H., Yang, B., Yang, Z., Lu, H., & Li, G. (2016). 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. Journal of Organic Chemistry, 81(17), 7654-7661. https://doi.org/10.1021/acs.joc.6b01385