Journal
TETRAHEDRON
Volume 67, Issue 6, Pages 1166-1170Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.12.002
Keywords
Cinchona ammonium catalyst; Aza Diels-Alder reaction
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Funding
- Ministry for Health, Welfare & family Affairs, Republic of Korea [A092006]
- Seoul RBD program [10541]
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Described is the efficiency of cinchona-derived quaternary ammonium salts as Lewis acid organo-catalysts in aza Diels-Alder reaction of Danishefsky's diene 1 with imines 2 and 16, providing 1,2-dialkyl-2,3-dihydro-4-pyridinones 3 and cyclic dihydropyridones 17, respectively. Among the nine of cinchonidine-derived quaternary ammonium catalysts prepared. N-2',3',4'-trifluorobenzyl-O-benzylcin-chonidinum bromide (6) exhibited the highest chemical yield (up to 99%). Systematic study on structure-catalytic efficiency relationship revealed that 2',3',4'-trifluorobenzyl, quinuclidine, and quinoline moieties are essential. (C) 2010 Elsevier Ltd. All rights reserved.
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