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Volumn 10, Issue 11, 2008, Pages 2291-2294

Novel N-phosphonio imine-catalyzed epoxidation reactions

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EID: 59849124628     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800690c     Document Type: Article
Times cited : (9)

References (41)
  • 2
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    • Special issue for organocatalysis: Chem. Rev. 2007, 107, 12.
    • (b) Special issue for organocatalysis: Chem. Rev. 2007, 107, 12.
  • 6
    • 0042980611 scopus 로고
    • For selective oxidation of sulfides: a
    • For selective oxidation of sulfides: (a) Davis, F. A.; Billmers, J. M. J. Org. Chem. 1983, 48, 2672.
    • (1983) J. Org. Chem , vol.48 , pp. 2672
    • Davis, F.A.1    Billmers, J.M.2
  • 15
    • 0000043848 scopus 로고
    • For oxidation of enolate anions: a
    • For oxidation of enolate anions: (a) Davis, F. A.; Chen, B.-C. Chem. Rev. 1992, 92, 919.
    • (1992) Chem. Rev , vol.92 , pp. 919
    • Davis, F.A.1    Chen, B.-C.2
  • 30
    • 59849117111 scopus 로고    scopus 로고
    • Although the highly electrophilic perfluorooxaziridines show the exceptionally strong oxidizing power, any catalytic oxidation reaction using corresponding imines have been reported: Petrov, V. A, Resnati, G. Chem. Rev. 1996, 96, 1
    • Although the highly electrophilic perfluorooxaziridines show the exceptionally strong oxidizing power, any catalytic oxidation reaction using corresponding imines have been reported: Petrov, V. A.; Resnati, G. Chem. Rev. 1996, 96, 1.
  • 36
    • 59849125293 scopus 로고    scopus 로고
    • A similar reactivity of N-trimethylsilylimine with sulfonylchlorides is already known: Georg, G. I.; Harriman, G. C. B.; Peterson, S. A. J. Org. Chem. 1992, 57, 1224.
    • A similar reactivity of N-trimethylsilylimine with sulfonylchlorides is already known: Georg, G. I.; Harriman, G. C. B.; Peterson, S. A. J. Org. Chem. 1992, 57, 1224.
  • 37
    • 59849125860 scopus 로고    scopus 로고
    • 3CN, compound 4a was obtained as a yellow powder (50%).
    • 3CN, compound 4a was obtained as a yellow powder (50%).
  • 38
    • 59849114653 scopus 로고    scopus 로고
    • 2O at -30°C (74%).
    • 2O at -30°C (74%).
  • 39
    • 59849098790 scopus 로고    scopus 로고
    • 2 (1 mL) was added, at rt, a solution of m-chloroperbenzoic acid (129.5 mg, 0.75 mmol). After 3 h, the solution was filtrated, and the evaporation of the solvent gave the corresponding oxaziridine 6a (41%).
    • 2 (1 mL) was added, at rt, a solution of m-chloroperbenzoic acid (129.5 mg, 0.75 mmol). After 3 h, the solution was filtrated, and the evaporation of the solvent gave the corresponding oxaziridine 6a (41%).
  • 40
    • 59849106529 scopus 로고    scopus 로고
    • 1H NMR to determine the conversion of the olefin into the corresponding epoxide.
    • 1H NMR to determine the conversion of the olefin into the corresponding epoxide.
  • 41
    • 59849122642 scopus 로고    scopus 로고
    • Probably due to the slow decompositon of oxone at rt, the epoxidation reaction is more efficient at 0°C.
    • Probably due to the slow decompositon of oxone at rt, the epoxidation reaction is more efficient at 0°C.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.