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Volumn 9, Issue 2, 2007, Pages 255-257

Asymmetric hydrogenation of α-chloro aromatic ketones catalyzed by η6-arene/TsDPEN-ruthenium(II) complexes

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC HYDROCARBON; KETONE; ORGANOMETALLIC COMPOUND; RUTHENIUM;

EID: 33846628216     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062661s     Document Type: Article
Times cited : (162)

References (37)
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    • Itsuno, S.1
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    • Jacobsen, E. N, Pfaltz, A, Yamamoto, H, Eds, Springer: Berlin
    • (b) Itsuno, S. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 1, pp 289-315.
    • (1999) Comprehensive Asymmetric Catalysis , vol.1 , pp. 289-315
    • Itsuno, S.1
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    • Jacobsen, E. N, Pfaltz, A, Yamamoto, H, Eds, Springer: Berlin
    • (d) Ohkuma, T.; Noyori, R. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 2004; Supplement 2, pp 7-19.
    • (2004) Comprehensive Asymmetric Catalysis , Issue.SUPPL.EMENT 2 , pp. 7-19
    • Ohkuma, T.1    Noyori, R.2
  • 17
    • 0033546106 scopus 로고    scopus 로고
    • Hydrogenation of 2,4′-dichloroacetophenone with chiral amidophosphine-phosphinite/Rh catalysts afforded the chiral alcohol in up to 68% ee. See: Devocelle, M.; Mortreux, A.; Agbossou, F. D. J.-R. Tetrahedron Lett. 1999, 40, 4551-4554.
    • Hydrogenation of 2,4′-dichloroacetophenone with chiral amidophosphine-phosphinite/Rh catalysts afforded the chiral alcohol in up to 68% ee. See: Devocelle, M.; Mortreux, A.; Agbossou, F. D. J.-R. Tetrahedron Lett. 1999, 40, 4551-4554.
  • 19
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    • For asymmetric hydrogenation of 1-tetralones catalyzed by BINAP/chiral 1,4-diamine-Ru catalysts, see: Ohkuma, T.; Hattori, T.; Ooka, H.; Inoue, T.; Noyori, R. Org. Lett. 2004, 6, 2681-2683.
    • For asymmetric hydrogenation of 1-tetralones catalyzed by BINAP/chiral 1,4-diamine-Ru catalysts, see: Ohkuma, T.; Hattori, T.; Ooka, H.; Inoue, T.; Noyori, R. Org. Lett. 2004, 6, 2681-2683.
  • 20
    • 20444437938 scopus 로고    scopus 로고
    • BINAP/picolylamine-Ru catalysts are effective for asymmetric hydrogenation of sterically hindered tert-alkyl ketones: Ohkuma, T.; Sandoval, C. A.; Srinivasan, R.; Lin, Q.; Wei, Y.; Muñiz, K.; Noyori, R. J. Am. Chem. Soc. 2005, 127, 8288-8289.
    • BINAP/picolylamine-Ru catalysts are effective for asymmetric hydrogenation of sterically hindered tert-alkyl ketones: Ohkuma, T.; Sandoval, C. A.; Srinivasan, R.; Lin, Q.; Wei, Y.; Muñiz, K.; Noyori, R. J. Am. Chem. Soc. 2005, 127, 8288-8289.
  • 22
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    • α-Chloroacetophenone suffers Darzens-like condensation in a basic alcoholic solvent: (a) Wasserman, H. H.; Aubrey, N. E.; Zimmerman, H. E. J. Am. Chem. Soc. 1953, 75, 96-98.
    • α-Chloroacetophenone suffers Darzens-like condensation in a basic alcoholic solvent: (a) Wasserman, H. H.; Aubrey, N. E.; Zimmerman, H. E. J. Am. Chem. Soc. 1953, 75, 96-98.
  • 25
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    • 6-arene/TsDPEN-Ru(II) complexes, see: (a) Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97-102.
    • 6-arene/TsDPEN-Ru(II) complexes, see: (a) Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97-102.
  • 28
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    • For mechanistic studies on asymmetric hydrogenation of ketones with BINAP/1,2-diamine-Ru catalysts, see: (a) Sandoval, C. A.; Ohkuma, T.; Muñiz, K.; Noyori, R. J. Am. Chem. Soc. 2003, 125, 13490-13503.
    • For mechanistic studies on asymmetric hydrogenation of ketones with BINAP/1,2-diamine-Ru catalysts, see: (a) Sandoval, C. A.; Ohkuma, T.; Muñiz, K.; Noyori, R. J. Am. Chem. Soc. 2003, 125, 13490-13503.
  • 31
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    • Characterization of the amino alcohol 5 was done after conversion to the triacetylated compound due to instability of 5 at ambient temperature (see Supporting Information).
    • Characterization of the amino alcohol 5 was done after conversion to the triacetylated compound due to instability of 5 at ambient temperature (see Supporting Information).
  • 35
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    • Hashimoto, N.; Itoh, N.; Ieda, S.; Kanda, A.; Baba, Y.; Ishibashi, N.; Okawa, K. WO 03/035600 A1, 2003; Chem. Abstr. 2003, 138, 353677.
    • (b) Hashimoto, N.; Itoh, N.; Ieda, S.; Kanda, A.; Baba, Y.; Ishibashi, N.; Okawa, K. WO 03/035600 A1, 2003; Chem. Abstr. 2003, 138, 353677.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.