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Volumn 45, Issue 1, 2004, Pages 75-78

Asymmetric construction of quaternary carbon centers by titanium-mediated stereospecific allylation of 2,3-epoxy alcohol derivatives

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; CARBON; EPOXIDE; HALIDE; MAGNESIUM CHLORIDE; REAGENT; TITANIUM;

EID: 0742269839     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.10.112     Document Type: Article
Times cited : (11)

References (51)
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    • The only reaction reported to date is that using organoaluminum reagents, see:
    • The only reaction reported to date is that using organoaluminum reagents, see: Hamilton R.J., Mander L.N. Aust. J. Chem. 44:1991;927-938.
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    • For the epoxide cleavage at the allylic or benzylic position by titanium reagents prepared by chlorotitanium triisopropoxide, see: Berlin: Springer. pp. 218-219
    • For the epoxide cleavage at the allylic or benzylic position by titanium reagents prepared by chlorotitanium triisopropoxide, see: Reetz M.T. Organotitanium Reagents in Organic Synthesis. 1986;Springer, Berlin. pp. 218-219.
    • (1986) Organotitanium Reagents in Organic Synthesis
    • Reetz, M.T.1
  • 23
    • 0001615493 scopus 로고
    • Stereoselective reactions of cyclic epoxides such as substituted cyclohexene oxides with a titanium reagent were already reported, see Refs. [5] and [6b]. See also
    • Stereoselective reactions of cyclic epoxides such as substituted cyclohexene oxides with a titanium reagent were already reported, see Refs. [5] and [6b]. See also, Blandy C., Choukroun R., Gervais D. Tetrahedron Lett. 24:1983;4189-4192.
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    • Blandy, C.1    Choukroun, R.2    Gervais, D.3
  • 26
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    • For titanium-mediated stereospecific ring-opening reactions of 2,3-epoxy alcohol derivatives, see:
    • For titanium-mediated stereospecific ring-opening reactions of 2,3-epoxy alcohol derivatives, see: Caron M., Sharpless K.B. J. Org. Chem. 50:1985;1557-1560.
    • (1985) J. Org. Chem. , vol.50 , pp. 1557-1560
    • Caron, M.1    Sharpless, K.B.2
  • 33
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    • For the reaction with 3-unsubstituted 2,3-epoxy alcohol derivatives, see (h):
    • For the reaction with 3-unsubstituted 2,3-epoxy alcohol derivatives, see (h): Ko S.Y., Sharpless K.B. J. Org. Chem. 51:1986;5413-5415.
    • (1986) J. Org. Chem. , vol.51 , pp. 5413-5415
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  • 34
    • 0007312102 scopus 로고
    • For titanium-mediated stereospecific ring-opening reactions of other acyclic epoxides, see:
    • For titanium-mediated stereospecific ring-opening reactions of other acyclic epoxides, see: Sutowardoyo K., Emziane M., Sinou D. Tetrahedron Lett. 30:1989;4673-4676.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 4673-4676
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  • 44
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    • Diethylaluminum azide-mediated anti selective ring-opening reaction of 3,3-disubstituted 2,3-epoxy alcohols to give azidohydrins was recently reported, see (f):
    • Diethylaluminum azide-mediated anti selective ring-opening reaction of 3,3-disubstituted 2,3-epoxy alcohols to give azidohydrins was recently reported, see (f): Davis C.E., Bailey J.L., Lockner J.W., Coates R.M. J. Org. Chem. 68:2003;75-82.
    • (2003) J. Org. Chem. , vol.68 , pp. 75-82
    • Davis, C.E.1    Bailey, J.L.2    Lockner, J.W.3    Coates, R.M.4
  • 49
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    • Halohydrin is one of the representative side products irrespective of the Grignard reagent used, the stereochemistry of which is not determined. No regioisomer of the allylated product was detected in the reaction mixture
    • Halohydrin is one of the representative side products irrespective of the Grignard reagent used, the stereochemistry of which is not determined. No regioisomer of the allylated product was detected in the reaction mixture.
  • 50
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    • note
    • The stereochemistry of 8 was determined by NOE analysis of the corresponding lactone, which was obtained by ozonolysis followed by oxidation.
  • 51
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    • 4. After purification by silica gel chromatography, 1,3-diol having a chiral quaternary carbon center was obtained
    • 4. After purification by silica gel chromatography, 1,3-diol having a chiral quaternary carbon center was obtained.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.