N-(2-Nitro-benzenesulfonyl) activated L-tyrosine methyl ester has been directly N-alkylated under solid-liquid phase-transfer catalysis (SL-PTC) conditions and in a coordinating non-hydrogen bonding donor (non-HBD) solvent, which reduces through specific solvation the nucleophilicity of the oxy-anionic center of the N,O-dianion formed by action of an anhydrous inorganic carbonate.
Chemoselective N-alkylation of di-N,O-protected tyrosine through specific oxy-anion solvation by non-hydrogen bonding donor solvents / M. Penso, D. Albanese, D. Landini, V. Lupi, D. Scaletti. - In: SYNLETT. - ISSN 0936-5214. - 2006:5(2006), pp. 741-744.
Chemoselective N-alkylation of di-N,O-protected tyrosine through specific oxy-anion solvation by non-hydrogen bonding donor solvents
D. AlbaneseSecondo
;D. Landini;V. LupiPenultimo
;D. ScalettiUltimo
2006
Abstract
N-(2-Nitro-benzenesulfonyl) activated L-tyrosine methyl ester has been directly N-alkylated under solid-liquid phase-transfer catalysis (SL-PTC) conditions and in a coordinating non-hydrogen bonding donor (non-HBD) solvent, which reduces through specific solvation the nucleophilicity of the oxy-anionic center of the N,O-dianion formed by action of an anhydrous inorganic carbonate.
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