메뉴 건너뛰기




Volumn 69, Issue 27-28, 2013, Pages 5702-5709

Enantioselective fluoride ring opening of aziridines enabled by cooperative Lewis acid catalysis

Author keywords

Fluoroamine; Asymmetric catalysis; Aziridine opening; Cooperative catalysis; Fluorination

Indexed keywords

AMINE; AZIRIDINE DERIVATIVE; COBALT; FLUORIDE; FLUOROAMINE; LEWIS ACID; NUCLEOPHILE; PICOLINAMIDE; PIPERIDINE; TITANIUM; UNCLASSIFIED DRUG;

EID: 84878492381     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.01.062     Document Type: Article
Times cited : (90)

References (50)
  • 1
    • 1542375289 scopus 로고    scopus 로고
    • X.E. Hu Tetrahedron 60 2004 2701 2743
    • (2004) Tetrahedron , vol.60 , pp. 2701-2743
    • Hu, X.E.1
  • 24
    • 84867284719 scopus 로고    scopus 로고
    • For a review, see
    • For a review, see: J. Park, and S. Hong Chem. Soc. Rev. 41 2012 6931 6943
    • (2012) Chem. Soc. Rev. , vol.41 , pp. 6931-6943
    • Park, J.1    Hong, S.2
  • 30
    • 0034966829 scopus 로고    scopus 로고
    • Fluoride ring opening of aziridine trans-1d was not observed in this reaction. Based on literature precedent, this is expected to be a challenging substrate for ring opening by (salen)M
    • Fluoride ring opening of aziridine trans-1d was not observed in this reaction. Based on literature precedent, this is expected to be a challenging substrate for ring opening by (salen)M: B.D. Brandes, and E.N. Jacobsen Synlett 2001 1013 1015
    • (2001) Synlett , pp. 1013-1015
    • Brandes, B.D.1    Jacobsen, E.N.2
  • 32
    • 0037023482 scopus 로고    scopus 로고
    • Under the standard conditions using 1,4-dioxane as solvent in the presence of activated powdered 4 Å molecular sieves, reaction of 1a provided 2a in 68% yield and 80% ee, accompanied by oxazoline in 20% yield and 80% ee. Control experiments confirmed that the oxazoline did not arise from product 2a. In TBME, the yield and ee of the oxazoline side product were depressed. The asymmetric synthesis of oxazolines from alkenes in up to 92% ee using a stoichiometric chiral nitridomanganese has been described; however, this is believed to proceed through rearrangement of the enantioenriched aziridine, which does not apply to meso N-acyl aziridines
    • Under the standard conditions using 1,4-dioxane as solvent in the presence of activated powdered 4 Å molecular sieves, reaction of 1a provided 2a in 68% yield and 80% ee, accompanied by oxazoline in 20% yield and 80% ee. Control experiments confirmed that the oxazoline did not arise from product 2a. In TBME, the yield and ee of the oxazoline side product were depressed. The asymmetric synthesis of oxazolines from alkenes in up to 92% ee using a stoichiometric chiral nitridomanganese has been described; however, this is believed to proceed through rearrangement of the enantioenriched aziridine, which does not apply to meso N-acyl aziridines: M. Nishimura, S. Minakata, T. Takahashi, Y. Oderaotoshi, and M. Komatsu J. Org. Chem. 67 2002 2101 2110
    • (2002) J. Org. Chem. , vol.67 , pp. 2101-2110
    • Nishimura, M.1    Minakata, S.2    Takahashi, T.3    Oderaotoshi, Y.4    Komatsu, M.5
  • 38
    • 84878504675 scopus 로고    scopus 로고
    • CCDC 919698 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.