198836-40-7Relevant articles and documents
A facile rearrangement of N-alkyl, N-(0 or p-nitrophenylsulfonamide)- α-amino esters
Wilson, Michael W.,Ault-Justus, Stephanie E.,Hodges, John C.,Rubin, J. Ronald
, p. 1647 - 1656 (1999)
The N-alkylation of primary nitrophenylsulfonamides followed by removal of the nitrophenylsulfonamide moiety under nucleophilic conditions to provide secondary amines has become an established literature procedure. Application of this methodology with les
A facile method for the N-alkylated of α-amino esters
Bowman, W. Russell,Coghlan, Daniel R.
, p. 15787 - 15798 (2007/10/03)
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.