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.