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Volumn , Issue 22, 2000, Pages 3793-3797

Lithiation of cinnamyl chloride: Stereoselective synthesis of propargylic oxiranes and aziridines

Author keywords

Asymmetric synthesis; Cinnamyl chloride; Enynes; Imines; Ketones; Lithiation

Indexed keywords

AZIRIDINE DERIVATIVE; CARBONYL DERIVATIVE; CINNAMYL ALCOHOL; ETHYLENE OXIDE DERIVATIVE; IMINE; KETONE;

EID: 0033724610     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200011)2000:22<3793::AID-EJOC3793>3.0.CO;2-M     Document Type: Article
Times cited : (32)

References (31)
  • 1
    • 0032505237 scopus 로고    scopus 로고
    • [1a] Propargylic epoxides are useful precursors of homopropargylic alcohols, see: N. Bernard, F. Chemla, N. Normant, Tetrahedron Lett. 1998, 39, 6715-6718. -
    • (1998) Tetrahedron Lett. , vol.39 , pp. 6715-6718
    • Bernard, N.1    Chemla, F.2    Normant, N.3
  • 15
    • 0007141465 scopus 로고
    • Georg Thieme Verlag, Stuttgart, New York
    • [8b] U. H. Brinker, Methoden der Organischen Chemie (Hauben Weyl), Georg Thieme Verlag, Stuttgart, New York, 1989, Vol. E19b/Teil 1, pp. 337-663. -
    • (1989) Methoden der Organischen Chemie (Hauben Weyl) , vol.E19B , Issue.1 , pp. 337-663
    • Brinker, U.H.1
  • 18
    • 0007004011 scopus 로고    scopus 로고
    • note
    • The homocoupling reaction between cinnamyl chloride (α-attack) and its lithiated derivative (γ-attack) proceeded regioselectively so that the geometry about the C-C double bond remained unchanged in 2 and consequently in the chlorohydrin 3 and the epoxide 4 as well.
  • 19
    • 0000970350 scopus 로고
    • The chemical shift found for the olefinic proton of 5b (δ = 6.83) is in excellent agreement with the value estimated (δ = 6.81) for a Z geometry utilizing Simon's additive shielding parameters for the prediction of NMR shifts, as reported by U. E. Matter, C. Pascual, E. Pretsch, A. Pross, W. Simon, S. Sternhell, Tetrahedron 1969, 25, 691-697.
    • (1969) Tetrahedron , vol.25 , pp. 691-697
    • Matter, U.E.1    Pascual, C.2    Pretsch, E.3    Pross, A.4    Simon, W.5    Sternhell, S.6
  • 23
    • 0000110756 scopus 로고
    • The chloro substituent has been chosen as the "large" group on the basis of frontier molecular orbital arguments that the ligand with the lowest-lying σ* orbital, rather than the sterically most demanding group, is perpendicular to the carbonyl plane and anti to the attacking nucleophile (E. P. Lodge, C. H. Heathcock, J. Am. Chem. Soc. 1987, 109, 3353-3361).
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 3353-3361
    • Lodge, E.P.1    Heathcock, C.H.2
  • 24
    • 20544433165 scopus 로고
    • On the other hand, the chlorine atom has almost the same van der Waals volume as the methyl group (A. Bondi, J. Phys. Chem. 1964, 68, 441-451).
    • (1964) J. Phys. Chem. , vol.68 , pp. 441-451
    • Bondi, A.1
  • 26
    • 0007050698 scopus 로고    scopus 로고
    • note
    • The stereochemistries of epoxide 4e and aziridine 8c were confirmed on the basis of their NOESY spectra.
  • 28
    • 33947290993 scopus 로고
    • α-Halo imines can easily be synthesized from α-halo ketones and primary amines as reported: [17a] K. Taguchi, F. H. Westheimer, J. Org. Chem. 1971, 36, 1570-1572. -
    • (1971) J. Org. Chem. , vol.36 , pp. 1570-1572
    • Taguchi, K.1    Westheimer, F.H.2
  • 30
    • 0007004013 scopus 로고    scopus 로고
    • note
    • Chloro amines 7a-c, which are the probable intermediates en route to the formation of aziridines 8a-c, could not be isolated.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.