Efficient Synthesis of Chiral Amides of 2-(2′-Carboxyphenyl)-4-hydroxy­quinoline

摘要: On deprotonation by lithium bistrimethylsilylamide (LBTSA), 2-phthalimidoacetophenone (1) is quantitatively converted to 6H, 12H-isoindolo [2, 1-a]-6, 7a-dihydroxyquinolin-12-one (2) ; weaker bases proved much less effective. Thermal dehydration of 2 vinilogous imide 3, then the AlCl3-catalyzed aminolysis (1S)-arylethylamines afforded (IS)-amides 2-(2'-carboxyphenyl)-4-hydroxyquinolines (5-7). This sequence represents an efficient assembling novel chiral heterocycles, potentially useful in enantioselection as ligands or selectors. In situ prepared Pd(II) complexes 5-7 exhibited catalytic activity allylic alkylation 1, 3-diphenyt-1-acetoxyprop-2-ene (8) dimethylmalonate anion complex 7 highest (64%) enantiomeric excess 3-diphenyl-1-dimetylmalonylprop-2-ene (9).