N-Sulfonyl α-imino ester-derived chiral oxaziridines: catalytic asymmetric synthesis and application as a modular chiral organic oxidantElectronic supplementary information (ESI) available: Experimental procedures and characterization of compounds. See DOI: 10.1039/c7cc02502e

• Main Authors: Tanaka, Naoya, Tsutsumi, Ryosuke, Uraguchi, Daisuke, Ooi, Takashi
• Format: Journal Article
• Language: English
• Published: 27.06.2017
• ISSN: 1359-7345; 1364-548X
• DOI: 10.1039/c7cc02502e

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. A novel class of chiral N -sulfonyl oxaziridines is catalytically prepared and introduced for use as highly reactive and enantiospecific oxidants.