메뉴 건너뛰기




Volumn 68, Issue 21, 2003, Pages 8222-8231

Chiral hydroperoxides as oxygen source in the catalytic stereoselective epoxidation of allylic alcohols by sandwich-type polyoxometalates: Control of enantioselectivity through a metal-coordinated template

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST SELECTIVITY; COORDINATION REACTIONS; HYDROGEN PEROXIDE; OXIDATION; STEREOCHEMISTRY;

EID: 0142121745     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034923z     Document Type: Article
Times cited : (65)

References (60)
  • 7
    • 0013174618 scopus 로고    scopus 로고
    • Pope M.T., Müller A., Eds, Kluwer Academic Publisher Netherlands
    • (e) Finke, R. G. In Polyoxometalate Chemistry; Pope, M. T., Müller, A., Eds; Kluwer Academic Publisher: Netherlands, 2001; pp 363-390.
    • (2001) Polyoxometalate Chemistry , pp. 363-390
    • Finke, R.G.1
  • 32
    • 0037295718 scopus 로고    scopus 로고
    • For a recent review, see: Bolm, C. Coord. Chem. Rev. 2003, 237, 245-256.
    • (2003) Coord. Chem. Rev. , vol.237 , pp. 245-256
    • Bolm, C.1
  • 49
    • 0035943278 scopus 로고    scopus 로고
    • Only primary allylic alcohols were used in this asymmetric study because kinetic resolution of racemic secondary allylic alcohols has been shown to give poor results in metal-catalyzed asymmetric epoxidations, see: (a) Adam, W.; Humpf, H.-U.; Roschmann, K. J.; M.; Saha-Möller, C. R. J. Org. Chem. 2001, 66, 5796-5800.
    • (2001) J. Org. Chem. , vol.66 , pp. 5796-5800
    • Adam, W.1    Humpf, H.-U.2    Roschmann, K.J.M.3    Saha-Möller, C.R.4
  • 51
    • 0142119980 scopus 로고    scopus 로고
    • note
    • The resulting TADDOL was recovered in >95% yield by silica gel chromatography without loss of optical purity, from which TADOOH may be easily regenerated; see ref 13f.
  • 54
    • 0142119979 scopus 로고    scopus 로고
    • note
    • At this time, it would be too speculative to propose a definite structure for the vanadium(V)-centered POM template to rationalize the stereochemical course of the epoxidation.
  • 57
    • 0034814798 scopus 로고    scopus 로고
    • Trapping of such radicals in reactions with TBHP and a high oxidation potential POM is known; see: Khenkin, A. M.; Neumann, R. J. Am. Chem. Soc. 2001, 123, 6437-6438.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 6437-6438
    • Khenkin, A.M.1    Neumann, R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.