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. 2012 Mar 28;134(12):5440-3.
doi: 10.1021/ja211880s. Epub 2012 Mar 20.

Hf(IV)-catalyzed enantioselective epoxidation of N-alkenyl sulfonamides and N-tosyl imines

José Luis Olivares-Romero  1 , Zhi Li, Hisashi Yamamoto
Affiliations

Hf(IV)-catalyzed enantioselective epoxidation of N-alkenyl sulfonamides and N-tosyl imines

José Luis Olivares-Romero et al. J Am Chem Soc. .

Abstract

Asymmetric epoxidation of allylic and homoallylic amine derivatives catalyzed by Hf(IV)-bishydroxamic acid complexes is described. Under similar conditions, aldimine and ketimine produced oxaziridines. The sulfonyl group is demonstrated to be an effective directing group for these transformations.

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Figures

Chart 1
Chart 1. Epoxidation of Allylic Sulfonate, Sulfonamide, Sulfones.a,b
aIsolated yield after chromatographic purification. bEnantiomeric excess values were determined by chiral HPLC.
See this image and copyright information in PMC

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