Journal of Physical Organic Chemistry p. 341 - 347 (1996)
Update date:2022-08-16
Topics:
Mueller, Paul
Baud, Corine
Jacquier, Yvan
Moran, Mary
Naegeli, Ivo
The [Rh2(OAc)4]-catalyzed decomposition of NsN=IPh {[N-(p-nitrobenzenesulfonyl)imino]phenyliodinane} in the presence of olefins affords aziridines in yields of up to 85%. The aziridination of cis-hex-2-ene and cis-β-methylstyrene is stereospecific, but, cis-stilbene affords a 3:1 mixture of cis- and trans-aziridines in low yield. With chiral Rh(II) catalysts, optically active aziridines are formed having enantiomeric excesses of up to 73%. The NsN-IPh-[Rh2(OAc)4] system is also efficient for the allylic amination of olefins and for insertion into CH bonds, activated by phenyl or oxygen substituents.
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