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Volumn 54, Issue 35, 1998, Pages 10339-10348

Asymmetric desymmetrization of meso-tetrahydrofuran derivatives by highly enantiotopic selective C-H oxidation

Author keywords

[No Author keywords available]

Indexed keywords

TETRAHYDROFURAN DERIVATIVE; TETRAHYDROPYRAN DERIVATIVE;

EID: 0032572840     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00489-X     Document Type: Article
Times cited : (54)

References (29)
  • 1
    • 0003417469 scopus 로고
    • Pergamon Press, Oxford
    • 1. For the recent review for asymmetric oxidation, see: a) In "Comprehensive Organic Synthesis" ed by Trost, B. M., Pergamon Press, Oxford, 1991, Vol. 7.
    • (1991) Comprehensive Organic Synthesis , vol.7
    • Trost, B.M.1
  • 16
    • 0002578608 scopus 로고
    • ed by I. Ojima, VCH publishers, Inc., New York
    • c) Jacobsen, E. N. In "Catalytic Asymmetric Synthesis" ed by I. Ojima, VCH publishers, Inc., New York, (1993), pp 159-202.
    • (1993) Catalytic Asymmetric Synthesis , pp. 159-202
    • Jacobsen, E.N.1
  • 17
    • 0013525731 scopus 로고    scopus 로고
    • 5. A part of this study has been communicated: Miyafuji, A.; Katsuki, T. Synlett 1997, 836-838.
    • (1997) Synlett , pp. 836-838
    • Miyafuji, A.1    Katsuki, T.2
  • 18
    • 0000408342 scopus 로고
    • 6. 4-(t-Butyl)tetrahydropyran was synthesized according to the reported procedure: Bailey, W. F.; Bischoff, J. J. J. Org. Chem. 1985, 50, 3009-3010.
    • (1985) J. Org. Chem. , vol.50 , pp. 3009-3010
    • Bailey, W.F.1    Bischoff, J.J.2
  • 19
    • 0010483849 scopus 로고    scopus 로고
    • note
    • 7. Chlorobenzene has been found to be the best solvent for asymmetric benzylic oxidation using (salen)manganese(III) complex as a catalyst (reference 2b)
  • 22
    • 0010482684 scopus 로고    scopus 로고
    • note
    • 10. We can not exclude the possibility that the reaction starts with one electron-transfer from n-orbital to oxo species and the interaction of the resulting SOMO and C-H σ orbital stabilizes the transion state for proton abstraction step. However, the present discussion of the dihedral angle-substrate reactivity relationship can also be successfully applied to the reaction via one electron-transfer process and the twist-boat conformers are considered to be more reactive than chair conformer, also in this reaction pathway.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.