Heteroatom transfer to alkenes by N-protected-oxaziridines: new reaction pathways and products

A Novel One-Pot Procedure for the Stereoselective Synthesis of α-Hydroxy Esters from Ortho Esters

“…While enantioselective variants of this reaction, usually with (+)- or (−)-(camphorylsulfonyl)oxaziridine as the chiral oxygen source, suffer from moderate stereocontrol, good to excellent asymmetric inductions are achieved in diastereoselective α-oxidations of chirally modified amide or ester enolates . Disadvantages of the latter method are the incompatibility of the oxaziridine with some functional groups and the additional steps required to attach and remove the chiral auxiliary.…”

Asymmetric Catalytic Routes to Dialkyl Peroxides and Oxaziridines

“…A remarkably useful property of these heterocyclic compounds is the configurational stability of the nitrogen atom, due to the combined effects of the ring strain and the presence of the electron-withdrawing oxygen atom, so that it is possible to synthesize enantioenriched oxaziridines . During the past 30 years, chiral oxaziridines, especially the N -sulfonyl derivatives, commonly known as Davis reagents, have been successfully employed in several enantioselective oxidations, such as α-hydroxylation of enolates, oxidation of sulfides, selenides, alkenes, and sulfenimines. ,− In addition, the stereoselective photochemical rearrangement of various chiral oxaziridines affords chiral lactams, and dipolar cycloaddition to unsaturated compounds leads to chiral heterocyclic products …”

“…The most exploited strategy to access chiral oxaziridines consists of the oxidation of chiral imines with MCPBA or peroxymonosulfate (oxone). Acyclic imines usually afford mixtures of diastereoisomers that could be separated by fractional crystallization or chromatography, ,,− as reported in Scheme . The best diastereoselectivities have been generally achieved with cyclic substrates, even though, in most instances, recrystallization is required to obtain optically pure products. ,− …”

Three‐Membered Heterocycles. Structure and Reactivity

“…In isolated cases, oxaziridines can engage in epoxidation reactions, both in an intramolecular sense [792] and as a bimolecular event, as illustrated by the highyielding conversion of 1,1-diphenylethene (818, Scheme 2.116) into the corresponding epoxide (819) [793]. However, this reaction is not general, and it is usually carried out more conveniently using conventional epoxidation conditions.…”