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Addition reactions to chiral aziridine-2-carboxaldimine toward various enantiopure nitrogen-containing heterocycles |
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| Authors: | Heui-Yoon Noh Seong In Paek Hoseop Yun |
| Institution: | a Department of Chemistry, Hankuk University of Foreign Studies, Yongin, Kyunggi-Do 449-719, South Korea b Center for Bioactive Molecular Hybrids, Yonsei University, Seoul 120-749, South Korea c Department of Molecular Science and Technology, Ajou University, Suwon, 442-749, South Korea d Department of Chemistry, Interdisciplinary Program of Integrated Biotechnology, Sogang University, Seoul 121-742, South Korea |
| Abstract: | Chiral (2R,1′R)-(1′-phenylethyl)aziridine-2-carboxaldimine was utilized as a nitrogen-containing starting substrate for the preparation of various enantiopure nitrogen-containing heterocycles. The additions of nucleophiles including organomagnesium reagents, cyanotrimethylsilane and ketene acetal to the chiral (2R,1′R)-(1′-phenylethyl)aziridine-2-carboxaldimine proceeded in highly stereoselective manner via chelation controlled transition states. Subsequent treatment of adducts with triphosgene and NaH yielded 5-substituted-4-chloromethylimidazolidin-2-ones. This imine was also served as either aza-diene or aza-dienophile with olefin or diene to provide hetero-Diels-Alder adducts 2-aziridinylpiperidines or 1,2,3,4-tetrahydroquinolines. |
| Keywords: | Aziridine-2-carboxaldimine Addition Nucleophiles Hetero-Diels-Alder reaction |
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