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Synthesis 2002(15): 2174-2176
DOI: 10.1055/s-2002-34835
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

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

Zdenko Hameršak, Mladen Litvić, Dragan Šepac, Andreja Lesac, Zlata Raza, Vitomir Šunjić*
Ruder Bošković Institute, Bjenička c. 54, P.O.B. 180, 10002 Zagreb, Croatia
Fax: +385(1)4680195; e-Mail: sunjic@rudjer.irb.hr;
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Publication History

Received 5 April 2002
Publication Date:
21 October 2002 (online)

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Abstract

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 to vinilogous imide 3, then the AlCl3-catalyzed aminolysis by (1S)-arylethylamines afforded (1S)-amides of 2-(2′-carboxyphenyl)-4-hydroxyquinolines (5-7). This sequence represents an efficient assembling of novel chiral heterocycles, potentially useful in enantioselection as ligands or chiral selectors. In situ prepared Pd(II) complexes of 5-7 exhibited catalytic activity in allylic alkylation of 1,3-diphenyl-1-acetoxyprop-2-ene (8) by dimethylmalonate anion; the complex of 7 afforded the highest (64%) enantiomeric excess of 1,3-diphenyl-1-dimetylmalonylprop-2-ene (9).

Key words

quinolines - amides - stereoselective synthesis - alkylations - heterocycles