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Intramolecular reaction
About: Intramolecular reaction is a research topic. Over the lifetime, 5015 publications have been published within this topic receiving 138213 citations.
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TL;DR: In this article, a new intramolecular Lewis acid catalyzed hetero-Diels-Alder reaction of N-arylimines 5 with nonactivated olefins tethered to the 2-azadiene system was developed in order to prepare 1,2,3,4,4a,9,9a,l0-octahydroacridined erivatives 6.
Abstract: A new intramolecular Lewis acid catalyzed hetero-Diels-Alder reaction of N-arylimines 5 with nonactivated olefins tethered to the 2-azadiene system was developed in order to prepare 1,2,3,4,-4a,9,9a,l0-octahydroacridined erivatives 6. Both reactivity and cis/ trans selectivity of 6 were mainly dependent on the substitution pattern in the 3-position of the cyclization precursor 5. The type of Lewis acid plays only a minor role in determination of the cis/trans ratio. The synthetic utility of this new cyclization was increased by performing it as a one-pot reaction. Both absolute configuration and preferred conformation were assigned by detailed NMR studies.
47 citations
TL;DR: Using this procedure, the chiral quinoline moiety of the uncialamycin, a new enediyne natural product, is prepared and an intramolecular imino Diels-Alder reaction promoted with BF(3) affording substituted quinolines is described.
Abstract: We herein described an intramolecular imino Diels−Alder reaction promoted with BF3·OEt2/DDQ affording substituted quinolines. Using this procedure, we prepared the chiral quinoline moiety of the uncialamycin, a new enediyne natural product.
47 citations
TL;DR: A new type of effective chloroimination was reported that afforded 4-chloro-2-perfluoroalkyl quinolines from fluorinated imidoyl chlorides in high yields, the first achievement of oxidative addition-reductive elimination type C-Cl bond activation by chloropalladation.
47 citations
TL;DR: A stereoselective intramolecular 1,3-dipolar nitrone cycloaddition useful in the synthesis of chromanes is described and diastereoselectivities up to 22:1 could be achieved.
Abstract: A stereoselective intramolecular 1,3-dipolar nitrone cycloaddition useful in the synthesis of chromanes is described. The reaction relies on the use of a chiral auxiliary on the nitrone partner. Key to the success of the reaction is the choice of auxiliary and the choice of Lewis acid catalyst. Utilizing an auxiliary with a pendant coordinating group, and Zn(OTf)2 as the Lewis acid, diastereoselectivities up to 22:1 could be achieved.
47 citations
TL;DR: In this article, the intramolecular Diels-alder reactions of aldehydes 3a and 3b afford lactones 4 and 5, respectively, and the mechanism of the reactions is considered.
47 citations