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Volumn 9, Issue 1, 2007, Pages 105-108

RuCl3/PPh3: An efficient combination for the preparation of chiral 1,3-anti-diols through catalytic hydrogenation

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOPHOSPHORUS COMPOUND; RUTHENIUM CHLORIDE; RUTHENIUM DERIVATIVE; TRIPHENYLPHOSPHINE; WATER;

EID: 33846425344     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062631p     Document Type: Article
Times cited : (22)

References (48)
  • 3
    • 33644531590 scopus 로고    scopus 로고
    • For reviews on stereoselective synthesis of 1,3-diols, see: a
    • For reviews on stereoselective synthesis of 1,3-diols, see: (a) Bode, S. E.; Wolberg, M.; Müller, M. Synthesis 2006, 557.
    • (2006) Synthesis , pp. 557
    • Bode, S.E.1    Wolberg, M.2    Müller, M.3
  • 12
    • 33845278216 scopus 로고    scopus 로고
    • Ru catalysts: (a) Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Ohta, T.; Takaya, H.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 629.
    • Ru catalysts: (a) Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Ohta, T.; Takaya, H.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 629.
  • 23
    • 33846449210 scopus 로고    scopus 로고
    • Ni catalysts: (l) Ito, K.; Harada, T.; Tai, A.; Izumi, Y. Chem. Lett. 1979, 1049.
    • Ni catalysts: (l) Ito, K.; Harada, T.; Tai, A.; Izumi, Y. Chem. Lett. 1979, 1049.
  • 39
    • 37649026044 scopus 로고    scopus 로고
    • For reviews on asymmetric hydrogenation, see: a
    • For reviews on asymmetric hydrogenation, see: (a) Noyori, R.; Ohkuma, T. Angew. Chem., Int. Ed. 2001, 40, 40.
    • (2001) Angew. Chem., Int. Ed , vol.40 , pp. 40
    • Noyori, R.1    Ohkuma, T.2
  • 42
    • 0035953061 scopus 로고    scopus 로고
    • 3/chiral diphosphines, see: Madec, J.; Pfister, X.; Phansavath, P.; Ratovelomanana-Vidal, V.; Genêt, J.-P. Tetrahedron 2001, 57, 2563.
    • 3/chiral diphosphines, see: Madec, J.; Pfister, X.; Phansavath, P.; Ratovelomanana-Vidal, V.; Genêt, J.-P. Tetrahedron 2001, 57, 2563.
  • 46
    • 0028343856 scopus 로고    scopus 로고
    • For preparation of the [Ru(P*P)Br2] complexes using chiral diphosphines, see: Genet, J.-P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Caño de Andrade, M. C.; Laffite, J. A. Tetrahedron: Asymmetry 1994, 5, 665.
    • For preparation of the [Ru(P*P)Br2] complexes using chiral diphosphines, see: Genet, J.-P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Caño de Andrade, M. C.; Laffite, J. A. Tetrahedron: Asymmetry 1994, 5, 665.
  • 47
    • 33846417719 scopus 로고    scopus 로고
    • Compounds 1a-g were prepared from the corresponding enantiomerically pure β-hydroxyesters, through addition of alkyllithium reagents on the related Weinreb amides.
    • Compounds 1a-g were prepared from the corresponding enantiomerically pure β-hydroxyesters, through addition of alkyllithium reagents on the related Weinreb amides.
  • 48
    • 33846450358 scopus 로고    scopus 로고
    • 3 (5.2 mg, 20 μmol). The reaction vessel was placed in a stainless steel autoclave which was purged with hydrogen and pressurized to 10 bar. The autoclave was heated to 50°C by circulating thermostated water in the double wall, and magnetic stirring was started as soon as the required temperature was reached. After stirring for 24 h, the autoclave was cooled to room temperature. Hydrogen was vented, and the reaction mixture was concentrated in vacuo.
    • 3 (5.2 mg, 20 μmol). The reaction vessel was placed in a stainless steel autoclave which was purged with hydrogen and pressurized to 10 bar. The autoclave was heated to 50°C by circulating thermostated water in the double wall, and magnetic stirring was started as soon as the required temperature was reached. After stirring for 24 h, the autoclave was cooled to room temperature. Hydrogen was vented, and the reaction mixture was concentrated in vacuo.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.