Catalytic asymmetric heterogeneous aziridination using CuHY/bis(oxazoline): effect of reaction conditions on enantioselectivity

Taylor, S., Gullick, J., Galea, N., McMorn, P., Bethell, D., Bulman Page, P. C. B., Hancock, F. E., King, F., Willock, D. J. and Hutchings, G. 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

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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
Depositing User: Rachel Smith
Date Deposited: 21 Jun 2011 10:43
Last Modified: 13 Mar 2019 00:46
URI: https://ueaeprints.uea.ac.uk/id/eprint/32852
DOI:

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