Desymmetrization of metallated cyclohexadienes with chiral N-tert-butanesulfinyl imines |
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Authors: | Maji Modhu Sudan Fröhlich Roland Studer Armido |
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Affiliation: | NRW Graduate School of Chemistry and Fachbereich Chemie, Organisch-Chemisches Institut, Westf?lische Wilhelms-Universit?t, Münster, Germany. |
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Abstract: | This communication describes the desymmetrization of various achiral metallated cyclohexadienes with a series of chiral N-tert-butanesulfinyl imines. Depending on the metal used, either the symmetrical diene (dicyclohexadienyl-zinc) or the desymmetrized diene (cyclohexadienyl-MgCl) is obtained in a good regioselectivity with excellent diastereoselectivity. The products formed should be useful building blocks for natural product synthesis. The symmetrical 1,4-dienes are readily oxidized to the corresponding diarylmethylamine derivatives. |
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