TY - JOUR
T1 - 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
AU - Zhang, Haowei
AU - Yang, Bing
AU - Yang, Zhen
AU - Lu, Hongjian
AU - Li, Guigen
N1 - Funding Information:
We acknowledge the financial support from the National Natural Science Foundation of China (21332005) and the Robert A. Welch Foundation (D-1361).
Publisher Copyright:
© 2016 American Chemical Society.
PY - 2016/9/2
Y1 - 2016/9/2
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=84984874857&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.6b01385
DO - 10.1021/acs.joc.6b01385
M3 - Article
AN - SCOPUS:84984874857
VL - 81
SP - 7654
EP - 7661
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 17
ER -