Cinchona-derived ammonium salts-catalyzed aza Diels-Alder reaction of Danishefsky's diene with imines SCIE SCOPUS

Cited 22 time in WEB OF SCIENCE Cited 22 time in Scopus
Title
Cinchona-derived ammonium salts-catalyzed aza Diels-Alder reaction of Danishefsky's diene with imines
Author(s)
Park, Yohan; Park, Eunyoung; Jung, Hyojun; Lee, Yeon-Ju; Jew, Sang-sup; Park, Hyeung-geun
KIOST Author(s)
Lee, Yeon Ju(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
URI
https://sciwatch.kiost.ac.kr/handle/2020.kiost/3889
DOI
10.1016/j.tet.2010.12.002
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
Publisher
PERGAMON-ELSEVIER SCIENCE LTD
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