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Volumn 10, Issue 12, 1999, Pages 2417-2428

Enantioselective conjugate radical addition reactions mediated by chiral Lewis acid complexes of (R,R)-4,6-dibenzofurandiyl-2,2'-bis(4- phenyloxazoline) (DBFOX/Ph)

Author keywords

[No Author keywords available]

Indexed keywords

OXAZOLINE DERIVATIVE;

EID: 0033580750     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00238-4     Document Type: Article
Times cited : (65)

References (42)
  • 18
    • 0011034289 scopus 로고
    • Preparation of the 4,6-diiodide 12, dinitrile 13, and diethyl ester 14 of dibenzofuran has been previously described: Tsang, K. Y.; Diaz, H.; Graciani, N.; Kelly, J. W. J. Am. Chem. Soc. 1994, 116, 3988-4005. Elaboration of diacid 9, dinitrile 13, diester 14, and diimidate 15 to the desired dihydroxy diamide 11 or DBFOX 6 was prevented by marginal solubility of starting materials or reaction intermediates. (equation presented)
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 3988-4005
    • Tsang, K.Y.1    Diaz, H.2    Graciani, N.3    Kelly, J.W.4
  • 19
    • 0344185922 scopus 로고    scopus 로고
    • note
    • 3BnCl). The better solubility of the crude diacid 9, prepared from carboxylation, may account for this difference.
  • 20
    • 0344185920 scopus 로고    scopus 로고
    • note
    • (Diethylamino)sulfur trifluoride (DAST) is more stable and cheaper (US$2.76/mmol, Aldrich) than the Burgess reagent (US$10.38/mmol, Aldrich).
  • 22
    • 33947087514 scopus 로고
    • N2 mechanism to give methyl urethanes in good yield. See (a) Burgess, E. M.; Penton, H. R.; Taylor, E. A.; Williams, W. M. Organic Syntheses, Coll. Vol. 6 1988, 788-791; (b) Burgess, E. M.; Penton, H. R.; Taylor, E. A. J. Org. Chem. 1973, 38, 26-31.
    • (1973) J. Org. Chem. , vol.38 , pp. 26-31
    • Burgess, E.M.1    Penton, H.R.2    Taylor, E.A.3
  • 24
    • 0344185918 scopus 로고    scopus 로고
    • 3, rfx, 88%;
    • 3N.
  • 25
    • 0345048198 scopus 로고    scopus 로고
    • 2, 25°C;
    • 3N.
  • 26
    • 0345479695 scopus 로고    scopus 로고
    • 2;
    • 3N.
  • 27
    • 0344185917 scopus 로고    scopus 로고
    • 3CN, 80°C;
    • 3N.
  • 28
    • 0344185916 scopus 로고    scopus 로고
    • nBuLi; then 17, rfx;
    • 3N.
  • 29
    • 0345479694 scopus 로고    scopus 로고
    • 2O, then 18, 25°C;
    • 3N.
  • 30
    • 0345048196 scopus 로고    scopus 로고
    • 3N
    • 3N.
  • 31
    • 0344185915 scopus 로고    scopus 로고
    • note
    • 2 with the appropriate Ag(I) salt, AgCl or AgBr precipitated out immediately.
  • 32
    • 0000953079 scopus 로고
    • We are grateful to Professor X. Zhang, Penn State University, for suggesting this improved protocol. For double deprotonation see: (a) Haenel, M. W.; Jakubik, D.; Rothenburger, E.; Schroth, G. Chem. Ber. 1991, 124, 1705-1710; (b) Jean, F.; Melnyk, O.; Tartar, A. Tetrahedron Lett. 1995, 36, 7657-7660.
    • (1991) Chem. Ber. , vol.124 , pp. 1705-1710
    • Haenel, M.W.1    Jakubik, D.2    Rothenburger, E.3    Schroth, G.4
  • 33
    • 0028863954 scopus 로고
    • We are grateful to Professor X. Zhang, Penn State University, for suggesting this improved protocol. For double deprotonation see: (a) Haenel, M. W.; Jakubik, D.; Rothenburger, E.; Schroth, G. Chem. Ber. 1991, 124, 1705-1710; (b) Jean, F.; Melnyk, O.; Tartar, A. Tetrahedron Lett. 1995, 36, 7657-7660.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 7657-7660
    • Jean, F.1    Melnyk, O.2    Tartar, A.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.