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pubmed-article:16388622pubmed:abstractText[reactions: see text] A rhodium complex of N-heterocyclic carbene (NHC) has been developed for intra- and intermolecular [4 + 2] and intramolecular [5 + 2] cycloaddition reactions. This is the first use of a transition-metal NHC complex in a Diels-Alder-type reaction. For the intramolecular [4 + 2] cycloaddition reactions, all the dienynes studied were converted to their corresponding cycloadducts in 91-99% yields within 10 min. Moreover, up to 1900 turnovers have been obtained for the intramolecular [4 + 2] cycloaddition at 15-20 degrees C. For the intermolecular [4 + 2] cycloadditions, high yields (71-99%) of the corresponding cycloaddition products were obtained. The reaction time and yield were highly dependent upon the diene and the dienophile. For the intramolecular [5 + 2] cycloaddition reactions, all the alkyne vinylcyclopropanes studied were converted to their corresponding cycloadducts in 91-98% yields within 10 min. However, the catalytic system was not effective for an intermolecular [5 + 2] cycloaddition reaction.lld:pubmed
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pubmed-article:16388622pubmed:authorpubmed-author:ChoiSoo...lld:pubmed
pubmed-article:16388622pubmed:authorpubmed-author:LeeSang IckSIlld:pubmed
pubmed-article:16388622pubmed:authorpubmed-author:ChungYoung...lld:pubmed
pubmed-article:16388622pubmed:authorpubmed-author:JungIl GuIGlld:pubmed
pubmed-article:16388622pubmed:authorpubmed-author:ParkJi HoonJHlld:pubmed
pubmed-article:16388622pubmed:authorpubmed-author:LeeBun...lld:pubmed
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pubmed-article:16388622pubmed:pagination91-6lld:pubmed
pubmed-article:16388622pubmed:dateRevised2006-11-15lld:pubmed
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pubmed-article:16388622pubmed:year2006lld:pubmed
pubmed-article:16388622pubmed:articleTitleRhodium N-heterocyclic carbene-catalyzed [4 + 2] and [5 + 2] cycloaddition reactions.lld:pubmed
pubmed-article:16388622pubmed:affiliationIntelligent Textile System Research Center, Department of Chemistry, College of Natural Sciences, Seoul National University, Seoul 151-747, Korea.lld:pubmed
pubmed-article:16388622pubmed:publicationTypeJournal Articlelld:pubmed
pubmed-article:16388622pubmed:publicationTypeResearch Support, Non-U.S. Gov'tlld:pubmed