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Volumn 59, Issue 9, 2003, Pages 1453-1467

Regiochemical control of the ring opening of 1,2-epoxides by means of chelating processes. Part 15: Regioselectivity of the opening reactions with MeOH of remote O-substituted regio- and diastereoisomeric pyranosidic epoxides under condensed- and gas-phase operating conditions

Author keywords

Chelation; Epoxides; Gas phase reactions; Regioselectivity

Indexed keywords

EPOXIDE; HYDROXIDE; PYRANOSIDE;

EID: 0037463508     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00078-4     Document Type: Article
Times cited : (7)

References (38)
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    • 4, in the case of methanolysis)
    • 4, in the case of methanolysis).
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    • The C-1 and C-2 product nomenclature refers to the attacking site of the nucleophile, i.e. at the C(1) or C(2) oxirane carbon of epoxides 1-9, in accordance with the numbering scheme shown in Schemes 1 and 2
    • The C-1 and C-2 product nomenclature refers to the attacking site of the nucleophile, i.e. at the C(1) or C(2) oxirane carbon of epoxides 1-9, in accordance with the numbering scheme shown in Schemes 1 and 2.
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    • For other studies on the regioselectivity of the opening reactions of oxirane systems structurally related to epoxides 7 and 8, see: (a) Schulz, M.; Kluge, R.; Liebsch, S.; Lessig, J.; Halik, M.; Gadissa, F. Tetrahedron 1996, 52, 13151-13166. (b) Carret, G.; Grouiller, A.; Pacheco, H. Carbohydr. Res. 1982, 111, 59-66. (c) Picq, D.; Anker, D.; Pacheco, H. Tetrahedron Lett. 1981, 22, 4517-4520.
    • (1996) Tetrahedron , vol.52 , pp. 13151-13166
    • Schulz, M.1    Kluge, R.2    Liebsch, S.3    Lessig, J.4    Halik, M.5    Gadissa, F.6
  • 11
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    • For other studies on the regioselectivity of the opening reactions of oxirane systems structurally related to epoxides 7 and 8, see: (a) Schulz, M.; Kluge, R.; Liebsch, S.; Lessig, J.; Halik, M.; Gadissa, F. Tetrahedron 1996, 52, 13151-13166. (b) Carret, G.; Grouiller, A.; Pacheco, H. Carbohydr. Res. 1982, 111, 59-66. (c) Picq, D.; Anker, D.; Pacheco, H. Tetrahedron Lett. 1981, 22, 4517-4520.
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    • Carret, G.1    Grouiller, A.2    Pacheco, H.3
  • 12
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    • For other studies on the regioselectivity of the opening reactions of oxirane systems structurally related to epoxides 7 and 8, see: (a) Schulz, M.; Kluge, R.; Liebsch, S.; Lessig, J.; Halik, M.; Gadissa, F. Tetrahedron 1996, 52, 13151-13166. (b) Carret, G.; Grouiller, A.; Pacheco, H. Carbohydr. Res. 1982, 111, 59-66. (c) Picq, D.; Anker, D.; Pacheco, H. Tetrahedron Lett. 1981, 22, 4517-4520.
    • (1981) Tetrahedron Lett. , vol.22 , pp. 4517-4520
    • Picq, D.1    Anker, D.2    Pacheco, H.3
  • 13
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    • 4/MeOH) afforded a crude reaction product only containing the addition products, the HEs 12 and 13 (Table 2)
    • 4/MeOH) afforded a crude reaction product only containing the addition products, the HEs 12 and 13 (Table 2).
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    • +
    • +.
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    • Franklin, J. L., Ed.; Plenum, New York
    • (b) Ausloos, P. In Ion-Molecule Reactions; Franklin, J. L., Ed.; Plenum, New York, 1970.
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  • 27
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    • 15 nucleophilic attack on 35 can occur only at the C(1) oxirane carbon
    • 15 nucleophilic attack on 35 can occur only at the C(1) oxirane carbon.
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    • 2b
    • 2b.
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    • 5 Scheme 7), decidedly high regioselectivities are obtained
    • 5 Scheme 7), decidedly high regioselectivities are obtained.
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    • 2c
    • 2c.
  • 36
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    • The confirmed structure of HE 11 makes it possible to assign the regioisomeric structure to HE 10
    • The confirmed structure of HE 11 makes it possible to assign the regioisomeric structure to HE 10.
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    • 3.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.