Efficient synthesis of alpha-aryl-/heteroaryl-substituted beta-amino acids via Ni(II) complex through the Suzuki coupling reaction.
We described a synthesis method by first using chlorotrimethylsilane as the activator to brominate the Ni(II) complex of the beta-alanine Schiff's base [beta-AlaNi(II)PABA] 1 and developed it to prepare beta-amino acids 5. The procedure involves a Suzuki coupling reaction between boric acids and the bromoenone 2, followed by hydrogenation and hydrolysis. This is the first report of the application of the Ni (II) complex [beta-AlaNi(II)PABA], which represents an attractive route to afford alpha-aryl-/heteroaryl-substituted beta-amino acids.
Ding
Xiao
X
The Center for Drug Discovery and Design, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, Shanghai 201203, People's Republic of China.
Ye
Deju
D
Liu
Fang
F
Deng
Guanghui
G
Liu
Guannan
G
Luo
Xiaomin
X
Jiang
Hualiang
H
Liu
Hong
H
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds / Q000737:chemistry
D000596:Amino Acids; D009942:Organometallic Compounds; D014297:Trimethylsilyl Compounds; C039293:trimethylchlorosilane; D009532:Nickel