Abstract
Oxaziridines have emerged as powerful and elegant oxygen- and nitrogen-transfer agents for a broad array of nucleophiles, due to the remarkably high and tunable reactivities. However, the asymmetric catalysis involving oxaziridines is still in its infancy. Herein, this review aims to examine recent advances in the catalytic asymmetric transformations of oxaziridines, including oxidation, amination, cycloaddition and deracemization.
Highlights
Oxaziridines, discovered in the mid-fifties by Emmons, are electrophilic three-membered heterocycles containing oxygen, nitrogen and carbon atoms [1]
The optically active and synthetically accessible oxaziridines [20,21] have emerged as crucial chiral building blocks in natural products and versatile enantiopure organic substrates in several enantioselective transformations, such as oxidation and amination, as well as some intriguing cycloaddition reactions with a large number of alkenes or alkynes to generate a diverse range of five-membered ring heterocycles
The [(3,3-dimethoxycamphoryl)sulfonyl]imine 18, the precursor of the Davis reagent, was subjected to the terminal oxidant hydrogen peroxide to afford the chiral oxidant in situ, which promoted the asymmetric sulfoxidation of dialkyl sulfides 16 with excellent enantioselectivities (Scheme 3) [39]
Summary
Oxaziridines, discovered in the mid-fifties by Emmons, are electrophilic three-membered heterocycles containing oxygen, nitrogen and carbon atoms [1] Due to their strained three-membered ring and the virtue of their relatively weak N-O bond, they exhibit unusually high and tunable reactivities and have received considerable attention from chemists. The optically active and synthetically accessible oxaziridines [20,21] have emerged as crucial chiral building blocks in natural products and versatile enantiopure organic substrates in several enantioselective transformations, such as oxidation and amination, as well as some intriguing cycloaddition reactions with a large number of alkenes or alkynes to generate a diverse range of five-membered ring heterocycles. The substrate-controlled and reagent-controlled asymmetric protocols are not pertinent for the present review
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