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Asymmetric aziridination by reaction of chiral N-sulfinylimines with sulfur ylides: Stereoselectivity improvement by use of tert-butylsulfinyl group as chiral auxiliary

✍ Scribed by JoséL García Ruano; Inmaculada Fernández; Miriam del Prado Catalina; Ana Alcudia Cruz

Publisher: Elsevier Science
Year: 1996
Tongue: English
Weight: 508 KB
Volume: 7
Category: Article
ISSN: 0957-4166
DOI: 10.1016/s0957-4166(96)00448-x

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✦ Synopsis

Chiral tert-butylsulfinyl group has been shown to be the chiral auxiliary of choice for the asymmetric aziridination of N-sulfinyliminas. Moreover, the sense of the asymmetric induction can be tuned in two ways: the chirality at the tert-butylsulfinyl Sulfur, or the nature of the methylene transfer reagent used. Thus, both aziridines 10(Ss,S) and 10(Rs,R), epimeric at C-2, were obtained in enantiomerically pure form by a single crystallisation (75% yield).

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