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Volumn 9, Issue 24, 1998, Pages 4341-4360

Asymmetric peroxidation of prochiral allylic and benzylic compounds with tert-butyl hydroperoxide and chiral bisoxazoline-copper complexes

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; BENZILIC ACID DERIVATIVE; COPPER COMPLEX; CYCLOHEXANE; CYCLOPENTENE DERIVATIVE; LIGAND; OXIDIZING AGENT; TERT BUTYL HYDROPEROXIDE;

EID: 0032564691     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00435-2     Document Type: Article
Times cited : (40)

References (52)
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    • Gadissa Gelalcha, F. Dissertation, Martin-Luther-Universität Halle-Wittenberg, 1998.
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    • Gadissa Gelalcha, F.1
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    • Kharasch, M. S.; Fono, A. J. Org. Chem. 1958, 23, 324-325; ibid. 1959, 24, 72-78.
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  • 14
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    • note
    • Compare Ref. 2; but in contrast, no peroxidation was observed, when isolated bis(aquo)-bis-(S)-prolinato copper(II) was employed.
  • 15
    • 0344626697 scopus 로고    scopus 로고
    • note
    • 1 Because this copper(I) complex is surely not involved in the peroxy-group transfer, the structure will not be discussed here.
  • 18
    • 0344626696 scopus 로고    scopus 로고
    • note
    • The same sign of optical rotation was also observed for the corresponding allylic alcohols and esters (compare refs. 2, 3, 27, 29 and 30).
  • 23
    • 0345488847 scopus 로고    scopus 로고
    • note
    • No peroxide formation was reported for the oxidation of cyclic olefins with t-BuOOH/HOAc in the presence of amino acid copper complexes (Ref. 2).
  • 24
    • 0344194895 scopus 로고    scopus 로고
    • note
    • A conceivable conversion 2→ 22 under the reaction conditions was excluded by independent experiments.
  • 31
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    • (a) Rieck, H.; Helmchen, G. Angew. Chem. 1995, 107, 2881-2883; Angew. Chem., Int. Ed. Engl. 1995, 34, 2687-2689.
    • (1995) Angew. Chem. , vol.107 , pp. 2881-2883
    • Rieck, H.1    Helmchen, G.2
  • 32
    • 0000110516 scopus 로고
    • (a) Rieck, H.; Helmchen, G. Angew. Chem. 1995, 107, 2881-2883; Angew. Chem., Int. Ed. Engl. 1995, 34, 2687-2689.
    • (1995) Angew. Chem., Int. Ed. Engl. , vol.34 , pp. 2687-2689
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    • Pretot, P.; Pfaltz, A. Angew. Chem. 1998, 110, 333-335; Angew. Chem., Int. Ed. Engl. 1998, 37, 323-325 and Refs. cited therein.
    • (1998) Angew. Chem. , vol.110 , pp. 333-335
    • Pretot, P.1    Pfaltz, A.2
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    • 0032536559 scopus 로고    scopus 로고
    • and Refs. cited therein
    • Pretot, P.; Pfaltz, A. Angew. Chem. 1998, 110, 333-335; Angew. Chem., Int. Ed. Engl. 1998, 37, 323-325 and Refs. cited therein.
    • (1998) Angew. Chem., Int. Ed. Engl. , vol.37 , pp. 323-325
  • 37
  • 41
    • 0031900123 scopus 로고    scopus 로고
    • (b) Wada, A.; Harata, M.; Hasegawa, K.; Jitsukawa, K.; Matsuda, H.; Mukai, M.; Kitagawa, T.; Einaga, H. Angew. Chem. 1998, 110, 874-875; Angew. Chem., Int. Ed. Engl. 1998, 37, 798-799.
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    • (b) Chaudhuri, P.; Hess, M.; Flörke, U.; Wieghardt, K. Angew. Chem. 1998, 110, 2340-2343; Angew. Chem., Int. Ed. Engl. 1998, 37, 2217-2220.
    • (1998) Angew. Chem., Int. Ed. Engl. , vol.37 , pp. 2217-2220
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    • For the pure enantiomers see: (a) Fukazawa, T.; Hashimoto, T. Tetrahedron: Asymmetry 1993, 4, 2323-2326. (b) Asami, M.; Ishizaki, T.; Inone, S. Tetrahedron: Asymmetry 1994, 5, 793-796.
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  • 48
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    • For the pure enantiomers see: (a) Fukazawa, T.; Hashimoto, T. Tetrahedron: Asymmetry 1993, 4, 2323-2326. (b) Asami, M.; Ishizaki, T.; Inone, S. Tetrahedron: Asymmetry 1994, 5, 793-796.
    • (1994) Tetrahedron: Asymmetry , vol.5 , pp. 793-796
    • Asami, M.1    Ishizaki, T.2    Inone, S.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.