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Volumn 76, Issue 2, 2008, Pages 1633-1645

Catalytic asymmetric synthesis of (-)-ritodrine hydrochloride via silyl enol ether amination using dirhodium(II) tetrakis [tetrafluorophaloyl-(S)-tert-leucinate]

Author keywords

( ) Ritodrine; Amination Reaction; Asymmetric Catalysis; Dirhodium(II) Complex; Silyl Enol Ether

Indexed keywords


EID: 61349160009     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-08-S(N)121     Document Type: Article
Times cited : (14)

References (80)
  • 11
    • 0013083033 scopus 로고    scopus 로고
    • For reviews, see: (a). Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds), Springer, Berlin
    • For reviews, see: (a). Shibasaki M., and Gröger H. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). 'Comprehensive Asymmetric Catalysis,' vol. III (1999), Springer, Berlin 1075-1090
    • (1999) 'Comprehensive Asymmetric Catalysis,' , vol.III , pp. 1075-1090
    • Shibasaki, M.1    Gröger, H.2
  • 44
    • 0000447921 scopus 로고    scopus 로고
    • For recent reviews on nitrene transfer reactions catalyzed by transition metal complexes, see: (a). Doyle M.P. (Ed), JAI Press, Greenwich
    • For recent reviews on nitrene transfer reactions catalyzed by transition metal complexes, see: (a). Muller P. In: Doyle M.P. (Ed). 'Advances in Catalytic Processes,' vol. II (1997), JAI Press, Greenwich 113-151
    • (1997) 'Advances in Catalytic Processes,' , vol.II , pp. 113-151
    • Muller, P.1
  • 45
    • 0000673216 scopus 로고    scopus 로고
    • Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds), Springer, Berlin
    • Jacobsen E.N. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). 'Comprehensive Asymmetric Catalysis,' vol. II (1999), Springer, Berlin 607-618
    • (1999) 'Comprehensive Asymmetric Catalysis,' , vol.II , pp. 607-618
    • Jacobsen, E.N.1
  • 49
    • 4544256467 scopus 로고    scopus 로고
    • Moss R.A., Platz M.S., and Jones Jr. M. (Eds), John Wiley & Sons, Hoboken
    • Doyle M.P. In: Moss R.A., Platz M.S., and Jones Jr. M. (Eds). 'Reactive Intermediate Chemistry,' (2004), John Wiley & Sons, Hoboken 561-592
    • (2004) 'Reactive Intermediate Chemistry,' , pp. 561-592
    • Doyle, M.P.1
  • 56
  • 59
    • 0029119899 scopus 로고
    • (a) For a review on the nitrophenylsulfonamide chemistry, see:
    • (a). Fukuyama T., Jow C.-K., and Cheung M. Tetrahedron Lett. 36 (1995) 6373 For a review on the nitrophenylsulfonamide chemistry, see:
    • (1995) Tetrahedron Lett. , vol.36 , pp. 6373
    • Fukuyama, T.1    Jow, C.-K.2    Cheung, M.3
  • 64
    • 0009142699 scopus 로고
    • For examples of stereoselective reduction of a-amino ketones, see: (a)
    • For examples of stereoselective reduction of a-amino ketones, see: (a). Fujita M., and Hiyama T. J. Org. Cherm. 53 (1988) 5415
    • (1988) J. Org. Cherm. , vol.53 , pp. 5415
    • Fujita, M.1    Hiyama, T.2
  • 68
    • 36049029718 scopus 로고    scopus 로고
    • 4, in which (E)-silylketene acetals were also found to be less reactive, see:
    • 4, in which (E)-silylketene acetals were also found to be less reactive, see:. Tanaka M., Kurosaki Y., Washio T., Anada M., and Hashimoto S. Tetrahedron Lett. 48 (2007) 8799
    • (2007) Tetrahedron Lett. , vol.48 , pp. 8799
    • Tanaka, M.1    Kurosaki, Y.2    Washio, T.3    Anada, M.4    Hashimoto, S.5
  • 73
    • 61349185393 scopus 로고    scopus 로고
    • Reduction of 5e with NaBH4 in EtOH at 0 °C afforded a 1.5:1 mixture of syn- and anti-amino alcohols in 92% yield.
    • Reduction of 5e with NaBH4 in EtOH at 0 °C afforded a 1.5:1 mixture of syn- and anti-amino alcohols in 92% yield.
  • 77
    • 61349131640 scopus 로고    scopus 로고
    • 3 (3 equiv.) in DMF at 23 °C met with little success (ca. 30% yield) due to the formation of substantial amounts (ca. 60% yield) of 4-benzyloxystyrene arising from the R-elimination.
    • 3 (3 equiv.) in DMF at 23 °C met with little success (ca. 30% yield) due to the formation of substantial amounts (ca. 60% yield) of 4-benzyloxystyrene arising from the R-elimination.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.