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Volumn 62, Issue 48, 2006, Pages 11145-11157

Reduction of substituted 1,10-phenanthrolines as a route to rigid chiral benzimidazolylidenes

Author keywords

Benzimidazolylidenes; Diastereoselective; N Heterocyclic carbenes; Phenanthrolines; Reduction

Indexed keywords

1,10 PHENANTHROLINE; ACETIC ACID; DIAMINE; IMIDAZOLIDINE DERIVATIVE; METHANOL; SOLVENT;

EID: 33750021145     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.09.023     Document Type: Article
Times cited : (21)

References (65)
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    • Reviews:
  • 17
    • 33750020572 scopus 로고    scopus 로고
    • For examples of oxazoline derived NHCs of the imidazolylidene series, see:
  • 25
    • 33749987762 scopus 로고    scopus 로고
    • note
    • The two possible exceptions are benzimidazolylidenes 5 and 6, which possess axial dissymmetry.
  • 29
    • 33749985446 scopus 로고    scopus 로고
    • Reviews:
  • 33
    • 33749996937 scopus 로고    scopus 로고
    • For reductions of N-alkyl pyridinium salts, see:
  • 46
    • 33749994964 scopus 로고    scopus 로고
    • note
    • With the exception of 2-isopropylphenanthroline and 2,9-diisopropylphenanthroline, all 2- and 2,9-substituted phenanthrolines have been previously reported. Neocuproine (2,9-dimethylphenanthroline) was purchased from Aldrich.
  • 52
    • 33750034131 scopus 로고    scopus 로고
    • note
    • It is concluded that diamine (-)-19f has the 2S,9S absolute configuration based on X-ray crystallographic analysis of 21a (Fig. 3).
  • 55
    • 0000894223 scopus 로고
    • Apart from steric or strain considerations, the lower yields of 27 and 29 may be a result of competing disproportionation reactions of intermediate dihydrophenanthrolines, as reported for dihydroquinolines. See:
    • Apart from steric or strain considerations, the lower yields of 27 and 29 may be a result of competing disproportionation reactions of intermediate dihydrophenanthrolines, as reported for dihydroquinolines. See:. Forrest T.P., Dauphinee G.A., and Deraniyagala S.A. Can. J. Chem. 63 (1985) 412
    • (1985) Can. J. Chem. , vol.63 , pp. 412
    • Forrest, T.P.1    Dauphinee, G.A.2    Deraniyagala, S.A.3
  • 56
    • 33750015013 scopus 로고    scopus 로고
    • note
    • See Supplementary data for COSY/NOESY spectra of 32 and 33.
  • 57
    • 33750027707 scopus 로고    scopus 로고
    • note
    • Crystals of rac-32 were used for X-ray determination, as it was not possible to obtain good crystals of (+)-32. The spectroscopic data for rac-32 were identical to optically active (+)-32, confirming that the compounds have the same relative stereochemistry.
  • 61
    • 33750020870 scopus 로고    scopus 로고
    • Prepared according to the procedure in: Morrison, R. C.; Hall, R. W.; Schwindeman, J. A.; Kamienski, C. W.; Engel, J. F. European Patent 0525881, 1993.
  • 62
    • 33749994709 scopus 로고    scopus 로고
    • Freshly prepared:
  • 65
    • 32044445819 scopus 로고    scopus 로고
    • Prepared by oxidation of commercially available (+)-endo-2-norborneol:
    • Prepared by oxidation of commercially available (+)-endo-2-norborneol:. Lattanzi A., Piccirillo S., and Scettri A. Eur. J. Org. Chem. (2006) 713
    • (2006) Eur. J. Org. Chem. , pp. 713
    • Lattanzi, A.1    Piccirillo, S.2    Scettri, A.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.