Tertiary amine-promoted enone aziridination: investigations into factors influencing enantioselective induction

A Armstrong, RDC Pullin, CR Jenner, K Foo…

Index: Armstrong, Alan; Pullin, Robert D. C.; Jenner, Chloe R.; Foo, Klement; White, Andrew J. P.; Scutt, James N. Tetrahedron Asymmetry, 2014 , vol. 25, # 1 p. 74 - 86

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Citation Number: 10

Abstract

Abstract trans-N-Unsubstituted aziridines were synthesised (up to 77% ee) via a chiral tertiary amine-promoted nucleophilic aziridination of α, β-unsaturated ketones utilising in situ generated N–N ylides (aminimines). A wide range of chiral tertiary amines were synthesised and evaluated, allowing structure–activity relationships to be drawn. The most efficient promoter for asymmetric aziridination, quinine, was assessed with several enones to ...