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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 paper, remote substituents that influence ground state state rotamer populations were found to be important controlling factors in the intramolecular Diels-Alder reaction with furan.
57 citations
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TL;DR: Submitting Ugi-adduct 4 to two consecutive metal-Catalyzed intramolecular reactions, namely copper-catalyzed O-arylation and palladium-catalystzed C-arylations of benzylic carbon affords the benzoxazolylisoindolinones in good to excellent yields.
Abstract: Submitting Ugi-adduct 4 to two consecutive metal-catalyzed intramolecular reactions, namely copper-catalyzed O-arylation and palladium-catalyzed C-arylation of benzylic carbon developed in the course of this study, affords the benzoxazolylisoindolinones in good to excellent yields.
57 citations
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TL;DR: The relative efficiencies of the twoprocesses are largely predictable and this combined with reasonable chemical and quantum yields make these photoreactions realistic synthetic procedures towards bicyclo[4.2.2] and tricyclo[3.3.0] octane systems as discussed by the authors.
Abstract: Dienophilic ethylenes yield solely ortho photocycloadducts with benzene whereas alkenes and enol ethers give products arising from both ortho and meta cycloaddition. The relative efficiencies of the twoprocesses are largely predictable and this combined with reasonable chemical and quantum yields make these photoreactions realistic synthetic procedures towards bicyclo[4.2.Oloctane and tricyclo[3.3.0.02'8]octane systems. The ortho cycloaddition involves a measure of charge—transfer to or from the ethylene at some stage in the reaction pathway, whereas two routes are considered to account for the orientational selectivity of the meta process involving ethylenes and substituted benzenes. Positions and modes of intramolecular reaction between the chromophores of non-conjugated phenyl vinyl bichromophoric systems are understandable in terms of their favoured molecular conformations leading to preferred orientations of the addends.
57 citations
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TL;DR: ABC analogues of the antitumor antibiotic lavendamycin were prepared via the palladium(0)-catalyzed cross-coupling reaction of various 2-haloheteroaromatics with 2-stannylated pyridines and quinolines using the Stille reaction, which efficiently provided several new heterobiaryl derivatives.
Abstract: ABC analogues of the antitumor antibiotic lavendamycin, which contain the key metal chelation site and redox-active quinone unit essential for biological activity, were prepared via the palladium(0)-catalyzed cross-coupling reaction of various 2-haloheteroaromatics with 2-stannylated pyridines and quinolines. Using the Stille reaction, 2-bromo substituted quinolines and 1-bromoisoquinolines were found to undergo efficient coupling with 2-pyridinylstannanes to provide unsymmetrical heterobiaryl derivatives. While the Stille reaction using the reverse coupling partners (i.e., 2-quinolinylstannanes and haloheteroaromatics) had not received much attention in the literature, we found that this alternative coupling reaction efficiently provided several new heterobiaryl derivatives. The gold-catalyzed intramolecular cycloisomerization of N-(prop-2-ynyl)-1H-indole-2-carboxamide smoothly afforded a β-carbolinone derivative that was subsequently used for a Pd(0)-catalyzed cross-coupling directed toward the synthesi...
57 citations
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TL;DR: The first total synthesis of the 15-membered ring cyclopeptide alkaloid abyssenine A 1 has been achieved with a longest linear sequence of 15 steps with the synthetic utility of copper-catalyzed coupling reactions.
Abstract: The first total synthesis of the 15-membered ring cyclopeptide alkaloid abyssenine A 1 has been achieved with a longest linear sequence of 15 steps. Central to the synthetic approach was an efficient copper-mediated Ullmann coupling/Claisen rearrangement sequence allowing for both ipso and ortho functionalization of aromatic iodide 4. This sequence was used for the synthesis of the aromatic core. The synthetic utility of copper-catalyzed coupling reactions was further demonstrated to install the enamide with a concomitant straightforward macrocyclization starting from acyclic alpha-amido-omega-vinyl iodide 13.
57 citations