N-(2-Nitrophenylsulfonyl)- (o-NBS-AA-OMe, 4) and N- (4-Nitrophenylsulfonyl)-alpha-amino acid methyl esters (p-NBS-AA-OMe, 5) were N-alkylated with a variety of alkyl halides 6 under solid-liquid phase-transfer catalysis (SL-PTC) conditions, affording the alkylated products o-NBS-N-R-2-AA-OMe 7 and p-NBS-N-R-2-AA-OMe 8 in excellent yields without any detectable racemization.
N-monoalkylation of alpha-amino acid esters under solid-liquid PTC conditions / D. Albanese, D. Landini, V. Lupi, M. Penso. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - :8(2000), pp. 1443-1449.
N-monoalkylation of alpha-amino acid esters under solid-liquid PTC conditions
D. AlbanesePrimo
;D. LandiniSecondo
;
2000
Abstract
N-(2-Nitrophenylsulfonyl)- (o-NBS-AA-OMe, 4) and N- (4-Nitrophenylsulfonyl)-alpha-amino acid methyl esters (p-NBS-AA-OMe, 5) were N-alkylated with a variety of alkyl halides 6 under solid-liquid phase-transfer catalysis (SL-PTC) conditions, affording the alkylated products o-NBS-N-R-2-AA-OMe 7 and p-NBS-N-R-2-AA-OMe 8 in excellent yields without any detectable racemization.
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