A METHOD FOR RHODIUM(II)-CATALYZED AZIRIDINATION OF OLEFINS

Authors
MULLER P BAUD C JACQUIER Y
Citation
P. Muller et al., A METHOD FOR RHODIUM(II)-CATALYZED AZIRIDINATION OF OLEFINS, Tetrahedron, 52(5), 1996, pp. 1543-1548
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
5
Year of publication
1996
Pages
1543 - 1548
Database
ISI
SICI code
0040-4020(1996)52:5<1543:AMFRAO>2.0.ZU;2-U
Abstract
The [Rh-2(OAc)(4)] catalyzed decomposition of (N-(p-nitrobenzenesulfon yl)imino)phenyliodinane (PhI=NNs) in the presence of olefins affords a ziridines In yields of 18-85%. The aziridination of cis-beta-methylsty rene (1h) and cis-hex-2-ene (1k) is stereospecific. However, with cis- stilbene (Im) a ca 3:1 mixture of cis- and trans aziridines 2m and 2l is obtained. With chiral catalysts asymmetric inductions in up to 73% ee are obtained.