Tetrahedron p. 15787 - 15798 (1997)
Update date:2022-07-30
Topics:
Bowman, W. Russell
Coghlan, Daniel R.
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.
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