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ToolsTaylor, Sophia, Gullick, John, Galea, Natasha, McMorn, Paul, Bethell, Donald, Bulman Page, Philip C., Hancock, Frederick E., King, Frank, Willock, David J. and Hutchings, Graham J. (2003) Catalytic asymmetric heterogeneous aziridination using CuHY/bis(oxazoline): effect of reaction conditions on enantioselectivity. Topics in Catalysis, 25 (1-4). pp. 81-88. ISSN 1022-5528
Full text not available from this repository. (Request a copy)Abstract
The copper-catalyzed aziridination of styrene with copper-exchanged zeolite HY(CuHY) and copper(II) triflate (trifluoromethanesulfonate) (Cu(OTf)(2)) as catalysts is described using N-(p-tolylsulfonyl) imino] phenyliodinane (PhI=NTs) as the nitrene donor. The effects on the ee and yield of the aziridine when the catalyst is modified by the presence of a chiral bis(oxazoline) are investigated in detail. The heterogeneously catalyzed reaction under these conditions shows a slight, but significant, enhancement in ee with increasing conversion at 25degreesC. This is not observed in the more rapid homogeneously catalyzed reaction under identical reaction conditions using PhINTs as the nitrene donor. The enhancement in ee is proposed to result from the preferential reaction of the (S)-aziridine with the Cu2+:bis(oxazoline) complex in the presence of PhI=NTs, leading to an enhancement of the (R)-aziridine in the remaining aziridine product.
| 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 09:43 |
| Last Modified: | 30 Sep 2021 03:44 |
| URI: | https://ueaeprints.uea.ac.uk/id/eprint/32852 |
| DOI: | 10.1023/B:TOCA.0000003100.56246.39 |
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