Highly enantioselective desymmetrization of aziridines with TMSNCS has been developed. Good yield and enantioselectivity were observed by using novel chiral imidazoline-phosphoric acid catalysts. The obtained product can be converted to a chiral β-aminothiol and a β-aminosulfonic acid.
Catalysts. -Good enantioselectivities are achieved using a novel BINOL-type catalyst for the reactions of aziridines with isothiocyanate (II) or thiobenzoic acid. The 2-pyridinesulfonyl group works as an efficient stereocontrolling group for the ring opening of aziridine. -(NAKAMURA*, S.; OHARA, M.; KOYARI, M.; HAYASHI, M.; HYODO, K.; NABISAHEB, N. R.; FUNAHASHI, Y.; Org. Lett. 16 (2014) 17, 4452-4455, http://dx.
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