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Volumn 32, Issue 4, 2003, Pages 354-355

Enantioselective aziridination and amination using p-toluenesulfonyl azide in the presence of Ru(salen)(CO) complex

Author keywords

[No Author keywords available]

Indexed keywords

2 TOLUENESULFONYLAZIDE; RUTHENIUM COMPLEX; TOLUENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0037487049     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2003.354     Document Type: Article
Times cited : (102)

References (27)
  • 4
    • 85039665261 scopus 로고    scopus 로고
    • ed. by E. N. Jacobsen, A. Pfaltz, and H. Yamamoto, Springer, Berlin, Chap. 17
    • b) E. N. Jacobsen, in "Comprehensive Asymmetric Catalysis II," ed. by E. N. Jacobsen, A. Pfaltz, and H. Yamamoto, Springer, Berlin (1999), Chap. 17.
    • (1999) Comprehensive Asymmetric Catalysis II
    • Jacobsen, E.N.1
  • 24
    • 85039659985 scopus 로고    scopus 로고
    • note
    • Typical experimental procedure is exemplified by the aziridination of styrene: under nitrogen atmosphere, a toluene solution (0.25 mL) of complex 1 (1.9 mg, 2 μmol) was concentrated twice azeotropically in vacuo. MS 4A (20 mg) and styrene (10.4 mg, 0.1 mmol) were added to the residue. To the mixture was added dichloromethane (0.5 mL) and the resulting suspension was stirred for 0.5 h at room temperature. To the suspension was added p-toluenesulfonyl azide (15.5 μL, 0.1 mmol) and stirred for 24 h. The reaction mixture was directly chromatographed on silica gel using hexane and ethyl acetate (hexane:ethyl acetate = 1/0-19/1-8/2) to give the corresponding aziridine (19.4 mg) in 71% yield. The enantiomeric excess of the product was determined by HPLC analysis using DAICEL CHIRALCEL OJ-H (hexane:i-PrOH = 1:1).
  • 26
    • 33751499952 scopus 로고
    • It has been reported that metal nitrenoid species undergoes aziridination and allylic C-H amination competitively: D. Evans, M. M. Faul, and M. T. Bilodeeau, J. Org. Chem., 56, 6744 (1991).
    • (1991) J. Org. Chem. , vol.56 , pp. 6744
    • Evans, D.1    Faul, M.M.2    Bilodeeau, M.T.3
  • 27
    • 0343597826 scopus 로고
    • A similar approaching model has been proposed for Mn(salen)-catalyzed epoxidation via the corresponding oxo manganese species: B. D. Brandes and E. N. Jacobsen, J. Org. Chem., 59, 4378 (1994).
    • (1994) J. Org. Chem. , vol.59 , pp. 4378
    • Brandes, B.D.1    Jacobsen, E.N.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.