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Topics in Catalysis

, Volume 25, Issue 1–4, pp 81–88 | Cite as

Catalytic Asymmetric Heterogeneous Aziridination Using CuHY/bis(oxazoline): Effect of Reaction Conditions on Enantioselectivity

  • Sophia Taylor
  • John Gullick
  • Natasha Galea
  • Paul McMorn
  • Donald Bethell
  • Philip C. Bulman Page
  • Frederick E. Hancock
  • Frank King
  • David J. Willock
  • Graham J. HutchingsEmail author
Article

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 25 °C. 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.

asymmetric heterogeneous catalysis aziridination of styrene bis (oxazoline)/zeolite catalysts 

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Copyright information

© Plenum Publishing Corporation 2003

Authors and Affiliations

  • Sophia Taylor
    • 1
  • John Gullick
    • 1
  • Natasha Galea
    • 1
  • Paul McMorn
    • 1
  • Donald Bethell
    • 2
  • Philip C. Bulman Page
    • 3
  • Frederick E. Hancock
    • 4
  • Frank King
    • 4
  • David J. Willock
    • 1
  • Graham J. Hutchings
    • 1
    Email author
  1. 1.Department of ChemistryCardiff UniversityCardiffUK
  2. 2.Leverhulme Centre for Innovative Catalysis, Department of ChemistryUniversity of LiverpoolLiverpoolUK
  3. 3.Department of ChemistryLoughborough UniversityLoughborough, LeicsUK
  4. 4.SynetixTeesideUK

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