Premium
Rhodium(II)‐catalyzed aziridinations and CH insertions with [ N ‐( p ‐nitrobenzenesulfonyl)imino]phenyliodinane
Author(s) -
Müller Paul,
Baud Corine,
Jacquier Yvan,
Moran Mary,
Nägeli Ivo
Publication year - 1996
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/(sici)1099-1395(199606)9:6<341::aid-poc791>3.0.co;2-5
Subject(s) - chemistry , allylic rearrangement , rhodium , amination , double bond , medicinal chemistry , catalysis , stereospecificity , yield (engineering) , enantiomer , enantiomeric excess , stereochemistry , enantioselective synthesis , organic chemistry , materials science , metallurgy
The [Rh 2 (OAc) 4 ]‐catalyzed decomposition of NsN(DOUBLE BOND)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(DOUBLE BOND)IPh‐[Rh 2 (OAc) 4 ] system is also efficient for the allylic amination of olefins and for insertion into CH bonds, activated by phenyl or oxygen substituents.