Microbial whole cell-catalyzed desymmetrization of prochiral malonamides: practical synthesis of enantioenriched functionalized carbamoylacetates and their application in the preparation of unusual α-amino acids

Catalyzed by Rhodococcus erythropolis AJ270, an amidase-containing microbial whole cell catalyst, under very mild conditions, a number of functionalized prochiral malonamides underwent enantioselective desymmetrization reaction to afford high yield of carbamoylacetic acids with moderate to excellent enantioselectivity. The synthetic application has been demonstrated with a multi-gram scale biocatalytic preparation of R-(−)-α-allyl-α-methyl-carbamoylacetic acid and its conversions to varied α,α-disubstituted α-amino acids of the interest of medicinal chemistry.