A facile method for the N-alkylated of α-amino esters

Article abstract of DOI:10.1016/S0040-4020(97)10015-1

Monoalkylation of the α-amino group of α-amino acid derivatives can be facilitated using 2 -and 4-nitrophenylsulfonamide intermediates. The nitrophenylsulfonamides of α-amino esters can be alkylated using an equimolar amount of carbonate base and a variety of alkyl bromides. Ready removal of the nitrophenylsulfonyl group is facilitated by S(N)Ar reaction between the N-alkylated sulfonamide and phenylthiolate to give the N-alkylated α-amino esters in good yield without racemisation of the chiral α-centres.