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Volumn 74, Issue 21, 2009, Pages 8377-8380

Asymmetric epoxidation of fluoroolefins by chiral dioxirane. Fluorine effect on enantioselectivity

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC EPOXIDATION; CHEMICAL EQUATIONS; FLUORINE EFFECT;

EID: 70350733543     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901553t     Document Type: Article
Times cited : (63)

References (60)
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  • 6
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    • For leading references on ketone 1, see: (a)
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    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 9806
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    • For leading references on ketone 2, see: (a)
    • For leading references on ketone 2, see: (a) Wu, X.-Y.; She, X.; Shi, Y. J. Am. Chem. Soc. 2002, 124, 8792.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 8792
    • Wu, X.-Y.1    She, X.2    Shi, Y.3
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    • 0034703736 scopus 로고    scopus 로고
    • For leading references on ketone 3, see: (a)
    • For leading references on ketone 3, see: (a) Tian, H.; She, X.; Shu, L.; Yu, H.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 11551
    • Tian, H.1    She, X.2    Shu, L.3    Yu, H.4    Shi, Y.5
  • 24
    • 0001564432 scopus 로고
    • For leading references on theoretic studies on transition states for the dioxirane epoxidation, see: (a)
    • For leading references on theoretic studies on transition states for the dioxirane epoxidation, see: (a) Bach, R. D.; Andrés, J. L.; Owensby, A. L.; Schlegel, H. B.; McDouall, J. J. W. J. Am. Chem. Soc. 1992, 114, 7207.
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    • Bach, R.D.1    Andrés, J.L.2    Owensby, A.L.3    Schlegel, H.B.4    McDouall, J.J.W.5
  • 31
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    • For examples of asymmetric epoxidation of fluoroallylic alcohols and nucleophilic epoxide opening, see: (a)
    • For examples of asymmetric epoxidation of fluoroallylic alcohols and nucleophilic epoxide opening, see: (a) Dubuffet, T.; Bidon, C.; Sauvêtre, R.; Normant, J.-F. J. Organomet. Chem. 1990, 393, 173.
    • (1990) J. Organomet. Chem. , vol.393 , pp. 173
    • Dubuffet, T.1    Bidon, C.2    Sauvêtre, R.3    Normant, J.-F.4
  • 35
    • 0010066603 scopus 로고
    • For examples of epoxidation of fluoroolefins, see: (a)
    • For examples of epoxidation of fluoroolefins, see: (a) Elkik, E.; Le Blanc, M. Bull. Soc. Chim. Fr. 1971, 38, 870.
    • (1971) Bull. Soc. Chim. Fr. , vol.38 , pp. 870
    • Elkik, E.1    Le Blanc, M.2
  • 42
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    • For examples of fluorinated epoxide synthesis by ring closure of halogenated alcohols, see: (a)
    • For examples of fluorinated epoxide synthesis by ring closure of halogenated alcohols, see: (a) Kirrmann, A.; Nouri-Bimorghi, R. Bull. Soc. Chim. Fr. 1972, 6, 2328.
    • (1972) Bull. Soc. Chim. Fr. , vol.6 , pp. 2328
    • Kirrmann, A.1    Nouri-Bimorghi, R.2
  • 48
    • 29544440489 scopus 로고
    • For an example of fluorinated epoxide synthesis by halogen substitution of chlorinated or brominated epoxides, see
    • For an example of fluorinated epoxide synthesis by halogen substitution of chlorinated or brominated epoxides, see: Leroy, J.; Bensoam, J.; Humiliere, M.; Wakselman, C.; Mathey, F. Tetrahedron 1980, 36, 1931.
    • (1980) Tetrahedron , vol.36 , pp. 1931
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  • 57
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    • note
    • The fluoroepoxides are reasonably stable except the epoxide from olefin 7, which readily decomposes on silica gel. The epoxides from olefins 5, and 11 are extremely volatile.
  • 58
    • 70350723721 scopus 로고    scopus 로고
    • The determination of the ee of compound 12 was attempted, but with no success
    • The determination of the ee of compound 12 was attempted, but with no success.
  • 59
    • 0030059390 scopus 로고    scopus 로고
    • The absolute configuration of 6-hydroxydecan-5-one is reported in
    • The absolute configuration of 6-hydroxydecan-5-one is reported in: Curci, R.; D'Accolti, L.; Dinoi, A.; Fusco, C.; Rosa, A. Tetrahedron Lett. 1996, 37, 115.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 115
    • Curci, R.1    D'Accolti, L.2    Dinoi, A.3    Fusco, C.4    Rosa, A.5
  • 60
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    • note
    • The van der Waals' radii of fluorine is larger than hydrogen (1.47 vs 1.20 Å) (see ref 7).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.