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Review
. 2018 Oct 16;23(10):2656.
doi: 10.3390/molecules23102656.

Recent Advances in the Catalytic Asymmetric Reactions of Oxaziridines

Qiao Ren  1 , Wen Yang  2 , Yunfei Lan  3 , Xurong Qin  4 , Youzhou He  5 , Lujiang Yuan  6
Affiliations
Review

Recent Advances in the Catalytic Asymmetric Reactions of Oxaziridines

Qiao Ren et al. Molecules. .

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.

Keywords: amination; aminohydroxylation; asymmetric catalysis; oxaziridines; oxidation.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Representative nonmetal organic oxidants.
Figure 2
Figure 2
Asynchronous transition state for oxygen atom transfer reaction [10].
Scheme 1
Scheme 1
Asymmetric epoxidation of alkenes mediated by biphenyl or binaphthyl catalysts.
Scheme 2
Scheme 2
Kinetic resolution of 2-substituted chromene substrates.
Scheme 3
Scheme 3
Enantioselective oxidation of sulfides.
Scheme 4
Scheme 4
Acid-promoted asymmetric oxidation of sulfides to sulfoxides.
Scheme 5
Scheme 5
Sulfoxidations with oxaziridinium 23.
Scheme 6
Scheme 6
Asymmetric synthesis of (R)-lansoprazole 25.
Scheme 7
Scheme 7
Titanium-catalyzed asymmetric hydroxylations.
Scheme 8
Scheme 8
Catalytic enantioselective hydroxylation of racemic malonates 30.
Scheme 9
Scheme 9
Catalytic asymmetric hydroxylation of N-nonsubstituted α-alkoxycarbonyl amide.
Scheme 10
Scheme 10
Enantioselective hydroxylation of 3-alkyl and 3-aryl-2-oxindoles.
Scheme 11
Scheme 11
Catalytic asymmetric hydroxylative dearomatization of 2-naphthols.
Scheme 12
Scheme 12
Chiral guanidine-catalyzed enantioselective α-hydroxylation.
Scheme 13
Scheme 13
Asymmetric catalytic α-hydroxylation reactions of β-keto esters.
Scheme 14
Scheme 14
Enantioselective α-hydroxylations of branched aldehydes.
Scheme 15
Scheme 15
Asymmetric catalytic Rubottom oxidation.
Scheme 16
Scheme 16
Ring expansion of donor-acceptor cyclopropane.
Scheme 17
Scheme 17
Oxaziridine-mediated enantioselective aminohydroxylation of styrenes 62.
Scheme 18
Scheme 18
Synthesis of enantioenriched 3-aminopyrroloindolines 67.
Scheme 19
Scheme 19
Iron catalyzed asymmetric aminohydroxylation of olefin 68.
Scheme 20
Scheme 20
Formal [3+2] cycloaddition reaction of ketenes and oxaziridines.
Scheme 21
Scheme 21
Mechanistic proposal for Lewis base-catalyzed cycloaddition.
Scheme 22
Scheme 22
Formal [3+2] cycloaddition of ammonium enolates with oxaziridines.
Scheme 23
Scheme 23
Asymmetric aminohydroxylation of azlactones with oxaziridines.
Scheme 24
Scheme 24
Deracemization of chiral sulfoxides.
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References

    1. Emmons W.D. The synthesis of oxaziridines. J. Am. Chem. Soc. 1956;78:6208–6209. doi: 10.1021/ja01604a072. - DOI
    1. Gao H., Zhou Z., Kwon D.-H., Coombs J., Jones S., Behnke N.E., Ess D.H., Kürti L. Rapid heteroatom transfer to arylmetals utilizing multifunctional reagent scaffolds. Nat. Chem. 2017;9:681–688. doi: 10.1038/nchem.2672. - DOI - PMC - PubMed
    1. Davis F.A., Chen B.-C. Asymmetric hydroxylation of enolates with N-sulfonyloxaziridines. Chem. Rev. 1992;92:919–934. doi: 10.1021/cr00013a008. - DOI
    1. Davis F.A., Reddy R.T., Han W., Reddy R.E. Asymmetric synthesis using N-sulfonyloxaziridines. Pure Appl. Chem. 1993;65:633–640. doi: 10.1351/pac199365040633. - DOI
    1. Davis F.A., Chen B.-C. Formation of C-O bonds by oxygenation of enolates. In: Helmchen G., Hoffman R.W., Mulzer J., Schaumann E., editors. Stereoselective Synthesis. Volume E21e. Georg Thieme Verlag; Stuttgart, Germany: 1995. p. 4497.

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