The regioselective α-alkylation of the benzophenone imine of glycinamide, alaninamide, and related derivatives
- 1 October 2006
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 84 (10) , 1301-1312
- https://doi.org/10.1139/v06-088
Abstract
The benzophenone imine of glycinamide was alkylated using ion pair extraction (RX, 10% aq. NaOH, Bu4NHSO4 (1 equiv.), CH2Cl2, rt) to give the α-monosubstituted products, which were then alkylated a second time using stronger basic conditions (KO-t-Bu, THF, 0 °C, RX). Crystal structures of the Schiff bases of glycinamide, an α-monosubstituted and an α,α-disubstituted product were reported.Key words: benzophenone imines, Schiff bases, alkylation, ion pair extraction (IPE), phase-transfer catalysis (PTC), anhydrous base, X-ray crystal structures.Keywords
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