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N-Sulfonyl α-imino ester-derived chiral oxaziridines: catalytic asymmetric synthesis and application as a modular chiral organic oxidant

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Abstract

A novel class of chiral N-sulfonyl oxaziridines is introduced for use as structurally modifiable chiral oxidants. These oxaziridines are readily prepared from N-sulfonyl α-imino esters in a highly enantioenriched form by oxidation with hydrogen peroxide using L-isoleucine-derived triaminoiminophosphorane as a catalyst. The distinct advantage of their structural modularity is demonstrated through the identification of an optimal oxaziridine that exhibits high reactivity and enantiospecificity in the asymmetric oxidation of a silyl enol ether and N-sulfonyl allylic and homoallylic amines.

Graphical abstract: N-Sulfonyl α-imino ester-derived chiral oxaziridines: catalytic asymmetric synthesis and application as a modular chiral organic oxidant

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Publication details

The article was received on 03 Apr 2017, accepted on 19 May 2017 and first published on 19 May 2017


Article type: Communication
DOI: 10.1039/C7CC02502E
Citation: Chem. Commun., 2017, Advance Article
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    N-Sulfonyl α-imino ester-derived chiral oxaziridines: catalytic asymmetric synthesis and application as a modular chiral organic oxidant

    N. Tanaka, R. Tsutsumi, D. Uraguchi and T. Ooi, Chem. Commun., 2017, Advance Article , DOI: 10.1039/C7CC02502E

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