Heterogeneous aziridination of styrene using [ N-( p-nitrophenylsulfonyl)imino]phenyliodinane as nitrene donor: influence of the reaction parameters on yield and enantioselectivity

The copper-catalysed aziridination of styrene with copper-exchanged zeolite Y (CuHY) and copper(II) triflate (Cu(OTf) 2) as catalysts is described and discussed. In particular, the effects of reaction conditions on the yield and enantiomeric excess of the aziridine product are described using [ N-(...

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Bibliographic Details
Published in:Journal of molecular catalysis. A, Chemical Chemical, 2002-05, Vol.182, p.571-575
Main Authors: Gullick, John, Taylor, Sophia, McMorn, Paul, Bethell, Donald, Bulman-Page, Philip C., Hancock, Frederick E., King, Frank, Hutchings, Graham J.
Format: Article
Language:English
Subjects:
Bis(oxazoline)-modified CuHY zeolite
Nitrene donors
Styrene aziridination
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Summary:The copper-catalysed aziridination of styrene with copper-exchanged zeolite Y (CuHY) and copper(II) triflate (Cu(OTf) 2) as catalysts is described and discussed. In particular, the effects of reaction conditions on the yield and enantiomeric excess of the aziridine product are described using [ N-( p-nitrophenylsulfonyl)imino]phenyliodinane (PhINNs) as nitrene donor. By careful control of the styrene:nitrene donor molar ratio and the solvent, an ee of 95% can be obtained for the heterogeneously catalysed bis(oxazoline)-modified zeolite CuHY. The ee achieved with the zeolite immobilised catalyst is significantly higher than that achieved for the non-immobilised homogeneous catalyst under comparable reaction conditions.
ISSN:1381-1169
1873-314X
DOI:10.1016/S1381-1169(01)00497-6