Addition reactions to chiral aziridine-2-carboxaldimine toward various enantiopure nitrogen-containing heterocycles

초록

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, cyanotrimethyl si lane 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. (c) 2005 Elsevier Ltd. All rights reserved.

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