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Volumn , Issue 12, 2004, Pages 2669-2673

New perfluoroalkyl-substituted bisoxazolines as chiral ligands in asymmetric CuII-catalyzed reactions

Author keywords

Biphasic catalysis; Chiral bisoxazolines; Fluorous ligands; Fluorous silica gel chromatography; Homogeneous catalysis

Indexed keywords

COPPER ION; LIGAND; OXAZOLINE DERIVATIVE; PERFLUORO COMPOUND; SILICA GEL;

EID: 4644239071     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400035     Document Type: Article
Times cited : (26)

References (36)
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    • Recently, an intense amount of research activity has been devoted to the immobilization of this class of compound on various supports, with the goal of recovering, and possibly recycling, the expensive chiral ligand. See: D. Rechavi, M. Lemaire, Chem. Rev. 2002, 702, 3467-3494.
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    • note
    • The enantiomeric excess of the product obtained when we employed Box 14 (91% ee) is similar to that reported in the literature (92% ee at 20 0C); see ref.[12)
  • 26
    • 4644374089 scopus 로고    scopus 로고
    • note
    • 2 complexes of ligands 4 and 6 were employed to catalyze the Diels-Alder cycloaddition between cyclopentadiene and A'-acryloyloxazolidinone, the corresponding cycloadducts were obtained with low ee; the chemical yield when using 6 was good, but it was very poor when using 4. [15] We note that this behavior is not a general feature of chiral fluorinated catalysts because in other cases they perform as efficiently as their non-fluorinated counterparts. See ref.131
  • 27
    • 0033832610 scopus 로고    scopus 로고
    • and references cited therein
    • For a recent discussion on the influence that the substitution pattern at the Box bridging carbon atom has on the steric course of Box-mediated asymmetric syntheses see: S. E. Denmark, C. M. Stiff, J. Org. Chem. 2000, 65, 5875-5878, and references cited therein.
    • (2000) J. Org. Chem. , vol.65 , pp. 5875-5878
    • Denmark, S.E.1    Stiff, C.M.2
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    • 11- promoted reactions, see: I. W Davies, R. J. Deeth, R. D. Larsen, P. J. Reider, Tetrahedron Lett. 1999, 40, 1233-1236.
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    • note
    • 11 complexes) did not afford satisfactory results.
  • 32
    • 0142011023 scopus 로고    scopus 로고
    • The separation, recovery, and recycling of a fluorous nickel catalyst using FSPE has been reported recently: B. Croxtall, E. G. Hope, A. M. Stuart, Chem. Commun. 2003, 2430-2431.
    • (2003) Chem. Commun. , pp. 2430-2431
    • Croxtall, B.1    Hope, E.G.2    Stuart, A.M.3
  • 33
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    • Fluorous silica was prepared according to a literature procedure: [21a] S. Kainz, Z. Y. Luo, D. P. Curran, W Leitner, Synthesis 1998, 1425-1527. For the use of fluorous silica as a solid support for fluorous catalyst, see ref. [3b]
    • (1998) Synthesis , pp. 1425-1527
    • Kainz, S.1    Luo, Z.Y.2    Curran, D.P.3    Leitner, W.4
  • 35
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    • [21b] C. C. Tzschuke, C. Markert, H. Glatz, W. Bannwarth, Angew. Chem. 2002, 114, 4678-4681; Angew. Chem. Int. Ed. 2002, 41, 4500-4503.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 4500-4503


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.