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- W2106135142 abstract "Lewis acid-catalyzed cyclization of proline-derived N-arylimines 8 gives the tetracyclic decahydro-7,7,11-trimethyl-in-dolizino[3,4-b]quinolines 17a, b in a ratio, which is highly dependent on the coordination number of the acidic catalyst. Whereas monodentate Brønsted and Lewis acids as well as octahedral bidentate Lewis acids preferably gave the all-trans product 17b, the all-cis product 17a was obtained by tetrahedral aluminium Lewis acids. In contrast to this chelation-controlled reversal of diastereoselectivity, mixtures of cis/trans undecahydro-6,6,10-trimethyl-11-azacyclopenta[a]-anthracenes 18b-e, h were isolated from the cyclization of the corresponding cyclopentane-derived N-arylimines 16 irrespective of the Lewis acid. Force field calculations support a stepwise iminium ion cyclization under thermodynamic control rather than a concerted hetero-Diels-Alder mechanism." @default.
- W2106135142 created "2016-06-24" @default.
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- W2106135142 date "1995-06-01" @default.
- W2106135142 modified "2023-09-26" @default.
- W2106135142 title "Chelation control by a second nitrogen atom in formal hetero Diels-Alder reactions ofN-arylimines" @default.
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- W2106135142 doi "https://doi.org/10.1002/jlac.1995199506140" @default.
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