Efficient synthesis of symmetrical alpha,alpha-disubstituted beta-amino acids and alpha,alpha-disubstituted aldehydes via dialkylation of nucleophilic beta-alanine equivalent.
Homologation of the nucleophilic beta-alanine equivalent beta-Ala Ni(II)-PABP [Ni(II) complex of beta-alanine Schiff base with 2-[N-(alpha-picolyl)amino]benzophenone (PABP), 1] via alkyl halide alkylation was systematically studied as a general method for preparing symmetrically alpha,alpha-disubstituted beta-amino acids. The dialkylation reactions could be easily performed and did not require inert atmosphere, dried solvents, and low temperatures, thereby affording the benefits of operationally convenient experimental procedure and high atom economy. Further, the methodology developed by us can also be used to generate symmetrical alpha,alpha-disubstituted aldehydes through an alternative decomposition method.
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.
Daizong
D
Lin
Guanghui
G
Deng
Jiang
J
Wang
Xiao
X
Ding
Hualiang
H
Jiang
Hong
H
Liu
D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D000478:Alkylation; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D012545:Schiff Bases / Q000737:chemistry*; D013237:Stereoisomerism; D015091:beta-Alanine / Q000737:chemistry*
D000447:Aldehydes; D000596:Amino Acids; D009942:Organometallic Compounds; D012545:Schiff Bases; D015091:beta-Alanine; D009532:Nickel