Cinchona-derived ammonium salts-catalyzed aza Diels-Alder reaction of Danishefsky's diene with imines SCIE SCOPUS
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- Title
- Cinchona-derived ammonium salts-catalyzed aza Diels-Alder reaction of Danishefsky's diene with imines
- KIOST Author(s)
- Lee, Yeon Ju(이연주)
- Alternative Author(s)
- 이연주
- Publication Year
- 2011-02-11
- Abstract
- 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.
- ISSN
- 0040-4020
- Bibliographic Citation
- TETRAHEDRON, v.67, no.6, pp.1166 - 1170, 2011
- Publisher
- PERGAMON-ELSEVIER SCIENCE LTD
- Subject
- PHASE-TRANSFER CATALYSTS; ALPHA-AMINO-ACIDS; ASYMMETRIC-SYNTHESIS; QUINOLINE DERIVATIVES; ALDOL REACTIONS; TRIFLATE; PYRIDINE; REAGENT; ESTERS; WATER
- Keywords
- Cinchona ammonium catalyst; Aza Diels-Alder reaction
- Type
- Article
- Language
- English
- Document Type
- Article
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- There are no files associated with this item.
