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- W2070196950 abstract "The highly diastereoselective synthesis of substituted 1,2,3,4,4a,9,9a,10-octahydroacridines 7, 8 with five stereogenic centers has been achieved by domino imine condensation/intramolecular polar [4π+ + 2π]-cycloaddition of anilines 3 and ω-unsaturated aldehydes 4. The transformations which can be performed under mild reaction conditions using 0.3 eq. BF3·Et2O as a Lewis acid give the cycloadducts 7, 8 with yields ranging from 63–76%. The relative configuration of 7, 8 was assigned by 1H- and 13C-NMR spectroscopy. For 7a, an X-ray crystal structure analysis was obtained. Experimental as well as semiempirical results support a polar [4π+ + 2π]-cycloaddition under kinetic control. It is assumed that the diastereoselectivity of the process is governed by decalin-like exo-E-anti-transition state structures 24, 25 with equatorial arrangement of the bulky substituents R2." @default.
- W2070196950 created "2016-06-24" @default.
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- W2070196950 date "1996-01-01" @default.
- W2070196950 modified "2023-09-23" @default.
- W2070196950 title "Domino imine condensation/intramolecular polar [4?+ + 2?]-cycloaddition of anilines and ?-unsaturated aldehydes: A versatile tool for the highly diastereoselective synthesis of 1,2,3,4,4a,9,9a,10-octahydroacridines" @default.
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- W2070196950 doi "https://doi.org/10.1002/prac.19963380189" @default.
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