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

✍ Scribed by W. Russell Bowman; Daniel R. Coghlan

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
853 KB
Volume
53
Category
Article
ISSN
0040-4020

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✦ Synopsis

Monoalkylation of the a-amino group of or-amino acid derivatives can be facilitated using 2and 4-nitrophenylsulfonamide intermediates. The nitrophenylsulfonamides of a-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 SNAr reaction between the N-alkylated sulfonamide and phenylthiolate to give the N-alkylated Or-amino esters in good yield without racemisation of the chiral cc-centres.

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