Synthesis of (S)-N-tert-butoxycarbonyl-N,O-isopropylidene-α- methylserinal: A potential building block for the asymmetric synthesis of non-natural amino acids

Article abstract of DOI:10.1016/S0040-4020(98)00937-5

The title compound (S)-α-methylserinal acetonide has been efficiently prepared from (S)-α-methylserine, which is readily available in enantiomerically pure form by Curtius rearrangement of α,α-dialkyl 2- cyanoesters obtained by diastereoselective alkylation of (1S,2R,4R)-10- dicyclohexylsulfamoylisobornyl 2-cyanopropanoate using methoxymethyl iodide or paraformaldehyde as electrophiles by an extension of our recently developed methodology for the synthesis of α,α-dialkylamino acids.