Application of MCR: facile one-pot diastereoselective syntheses of novel chiral alpha,alpha'-iminodiacetic acid analogues.
Several pairs of enantiomeric alpha,alpha'-iminodiacetic acid analogues (2 and 4) were prepared separately by highly diastereoselective 3CR, which involves a reaction of an isocyanide, an aldehyde, and an enantiomerically pure amino acid in methanol. Synthesis of each of the enantiomers was controlled by the configuration of the amino acid; L-amino acid produces one enantiomer and D-amino acid generates the other. The diastereoselectivity of the 3CR is very sensitive to the substituent size of both aldehyde and enantiomerically pure amino acid.
Sung
Kuangsen
K
Department of Chemistry, National Cheng Kung University, Tainan, Taiwan, ROC. kssung@mail.ncku.edu.tw
Chen
Fu-Lin
FL
Chung
Meng-Jung
MJ
D000447:Aldehydes / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry*; D003486:Cyanides / Q000737:chemistry; D007098:Imino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D000432:Methanol; D015394:Molecular Structure; D013237:Stereoisomerism
D000447:Aldehydes; D000596:Amino Acids; D003486:Cyanides; D007098:Imino Acids; C008109:iminodiacetic acid; D000432:Methanol