A diastereoselective Mannich-type reaction of α-fluorinated carboxylate esters: synthesis of β-amino acids containing α-quaternary fluorinated carbon centers.
We report a diastereoselective Mannich-type reaction of α-alkyl, α-aryl, and α-vinyl fluoroacetates with N-tert-butylsulfinyl imines. This method provides a powerful means to access a broad range of highly functionalized β-amino acids containing α-fluorinated quaternary stereogenic carbon centers. We also show that the stereochemical outcome of the present reaction is highly dependent on the steric and electronic properties of the fluorocarbon nucleophiles. This protocol uses readily available starting materials, tolerates a variety of functional groups, and is operationally simple.
Department of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, 333 Longteng Road, Shanghai, 201620, P. R. China. ya.li@sues.edu.cn.
Xiang
X
Li
Department of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, 333 Longteng Road, Shanghai, 201620, P. R. China. ya.li@sues.edu.cn.
Ya
Y
Li
Department of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, 333 Longteng Road, Shanghai, 201620, P. R. China. ya.li@sues.edu.cn.
Huaqi
H
Shang
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D004952:Esters / Q000737:chemistry*; D054879:Halogenation; D007097:Imines / Q000737:chemistry; D013237:Stereoisomerism
D000596:Amino Acids; D002264:Carboxylic Acids; D004952:Esters; D007097:Imines; D002244:Carbon