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ToolsTaylor, Sophia, Gullick, John, McMorn, Paul, Bethell, Donald, Bulman Page, Philip C., Hancock, Frederick E., King, Frank and Hutchings, Graham J. (2003) Catalytic asymmetric heterogeneous aziridination of styrene using CuHY/bis(oxazoline): comments on the factors controlling enantioselectivity. Topics in Catalysis, 24 (1-4). pp. 43-50. ISSN 1022-5528
Full text not available from this repository. (Request a copy)Abstract
The copper-catalyzed aziridination of styrene is described using both heterogeneous, copper-exchanged zeolite HY, and homogeneous, copper (II) triflate catalysts using both [N-(p-tolylsulfonyl)imino]phenyliodinane (PhI=NTs) and [N-(p-nosylsulfonyl)imino]phenyliodinane (PhI=NNs) as nitrene donors. The key differences observed for the two catalysts when modified by chiral bis(oxazoline) ligands are discussed in detail. In particular, the heterogeneously catalyzed asymmetric reaction can give much higher enantioselection than the comparable homogeneously catalyzed reaction. The structure of the bis(oxazoline) ligand is the critical factor, and bis(oxazoline) ligands that are ineffective with the homogeneous catalysts are highly effective for the Cu2+ cation constrained within the zeolite micropores. The consequences of this observation for the design of chiral ligands for asymmetric heterogeneous catalysis are discussed. The effect of the degree of styrene conversion on the enantioselectivity is described in detail using PhI=NNs as a nitrene donor. The reaction shows a significant enhancement in ee with conversion at 25degreesC, and the possible origin of this effect is discussed.
| Item Type: | Article |
|---|---|
| Faculty \ School: | Faculty of Science > School of Chemistry |
| UEA Research Groups: | Faculty of Science > Research Groups > Synthetic Chemistry (former - to 2017) Faculty of Science > Research Groups > Chemistry of Materials and Catalysis |
| Depositing User: | Rachel Smith |
| Date Deposited: | 21 Jun 2011 09:44 |
| Last Modified: | 11 Aug 2023 16:30 |
| URI: | https://ueaeprints.uea.ac.uk/id/eprint/32853 |
| DOI: | 10.1023/B:TOCA.0000003075.67883.4a |
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