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Volumn 37, Issue 1, 1996, Pages 25-28

A new practical asymmetric synthesis of C2-symmetrical 1,1′-ferrocenyl diols via CBS-reduction

Author keywords

[No Author keywords available]

Indexed keywords

FERROCENE DERIVATIVE;

EID: 0030027142     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02098-5     Document Type: Article
Times cited : (69)

References (28)
  • 3
    • 0000625373 scopus 로고
    • Hartley, F. R. (Ed.); Patai, S. (Series Ed.) Wiley: New York
    • (c) Brunner, H. in The Chemistry of the metal-carbon bond. Hartley, F. R. (Ed.); Patai, S. (Series Ed.) Wiley: New York, 1989, Vol. 5, p. 109.
    • (1989) The Chemistry of the Metal-carbon Bond , vol.5 , pp. 109
    • Brunner, H.1
  • 20
    • 0001064329 scopus 로고
    • In contrast, the addition of dialkylzincs to ferrocene -1,1′-dicarbaldehyde in the presence of a chiral catalyst proved to be very limited due to interactions of the alcoholate obtained after mono-addition and the remaining aldehyde function leading to low enantiomeric excess and considerable amounts of meso-diol (S. Vettel, unpublished results, Marburg 1994). Compare with a successful approach using N,N-dialkylnorephedrines as chiral catalysts: Soai, K.; Hayase, T.; Takai, K.; Sugiyama, T. J. Org. Chem. 1994, 59, 7908.
    • (1994) J. Org. Chem. , vol.59 , pp. 7908
    • Soai, K.1    Hayase, T.2    Takai, K.3    Sugiyama, T.4
  • 21
    • 85029988794 scopus 로고    scopus 로고
    • note
    • 13C-NMR spectroscopy).
  • 24
    • 85029990040 scopus 로고    scopus 로고
    • note
    • NMR-spectroscopy of the crude reaction mixture of 9b indicates ca. 95 % selectivity for the directed metallation. Recrystallization from t-BuOMe affords the pure enantiomer 9b.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.