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Rhodium(II)-catalyzed aziridinations and CH insertions with [N-(p-nitrobenzenesulfonyl)imino]phenyliodinane

✍ Scribed by Paul Müller; Corine Baud; Yvan Jacquier; Mary Moran; Ivo Nägeli

Book ID: 101285099
Publisher: John Wiley and Sons
Year: 1996
Tongue: English
Weight: 486 KB
Volume: 9
Category: Article
ISSN: 0894-3230
DOI: 10.1002/(sici)1099-1395(199606)9:6<341::aid-poc791>3.0.co;2-5

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✦ Synopsis

The [Rh,(OAc),]-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-pmethylstyrene is stereospecific, but, cis-stilbene affords a 3 : 1 mixture of cis-and trans-aziridines in low yield. With chiral Rh(I1) catalysts, optically active aziridines are formed having enantiomeric excesses of up to 73%. The NsN=IPh-[Rh,(OAc),] system is also efficient for the allylic amination of olefins and for insertion into CH bonds, activated by phenyl or oxygen substituents. 'Conditions: 1 mmol of NsN=IPh. 20 mmol of olefin, 0.02 mmol of [Rh,(OAc),] in CH,CI, (10 ml) in presence of molecular sieves 4A (6.0 g). room temperature.

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