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Volumn 128, Issue 51, 2006, Pages 16448-16449

Enantioselective reductive coupling of 1,3-enynes to heterocyclic aromatic aldehydes and ketones via rhodium-catalyzed asymmetric hydrogenation: Mechanistic insight into the role of Brønsted acid additives

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKENE; CARBON; DEUTERIUM; HETEROCYCLIC COMPOUND; HYDROGEN; KETONE; RHODIUM; SILICA GEL;

EID: 33845961272     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0673027     Document Type: Article
Times cited : (227)

References (53)
  • 1
    • 0003720729 scopus 로고
    • For selected reviews on alkene hydroformylation, see: a, Springer: Berlin
    • For selected reviews on alkene hydroformylation, see: (a) Falbe, J. Carbon Monoxide in Organic Synthesis: Springer: Berlin, 1970.
    • (1970) Carbon Monoxide in Organic Synthesis
    • Falbe, J.1
  • 7
    • 0000619084 scopus 로고    scopus 로고
    • Jacobsen, E. N, Pfaltz, A, Yamamoto, H, Eds, Springer-Verlag: Berlin
    • (g) Nozaki, K. In Comprehensive Asymmetric Catalysis: Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. 1, p 381.
    • (1999) Comprehensive Asymmetric Catalysis , vol.1 , pp. 381
    • Nozaki, K.1
  • 9
    • 0037176242 scopus 로고    scopus 로고
    • For hydrogen-mediated C-C bond formations developed in our lab, see: a
    • For hydrogen-mediated C-C bond formations developed in our lab, see: (a) Jang, H.-Y.; Huddleston, R. R.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 15156.
    • (2002) J. Am. Chem. Soc , vol.124 , pp. 15156
    • Jang, H.-Y.1    Huddleston, R.R.2    Krische, M.J.3
  • 24
    • 0000193074 scopus 로고    scopus 로고
    • Prior to our work, the following hydrogen-mediated C-C bond formations under CO-free conditions were reported: (a) Molander, G. A.; Hoberg, J. O. J. Am. Chem. Soc. 1992, 114, 3123.
    • Prior to our work, the following hydrogen-mediated C-C bond formations under CO-free conditions were reported: (a) Molander, G. A.; Hoberg, J. O. J. Am. Chem. Soc. 1992, 114, 3123.
  • 26
    • 0037467387 scopus 로고    scopus 로고
    • An enantioselective variant of Montgomery's Ni-catalyzed alkyne-aldehyde coupling has been reported. This transformation requires 20 mol, loadings of chiral ligand and syringe pump addition of reactants: Miller, K. M, Huang, W.-S, Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 3442
    • An enantioselective variant of Montgomery's Ni-catalyzed alkyne-aldehyde coupling has been reported. This transformation requires 20 mol % loadings of chiral ligand and syringe pump addition of reactants: Miller, K. M.; Huang, W.-S.; Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 3442.
  • 27
    • 0000463815 scopus 로고    scopus 로고
    • For reviews encompassing direct reductive coupling of alkynes to carbonyl partners, see: a
    • For reviews encompassing direct reductive coupling of alkynes to carbonyl partners, see: (a) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
    • (1996) Chem. Rev , vol.96 , pp. 635
    • Ojima, I.1    Tzamarioudaki, M.2    Li, Z.3    Donovan, R.J.4
  • 34
    • 84987584214 scopus 로고    scopus 로고
    • Alkyne-aldehyde coupling may he achieved indirectly via alkyne hydrometalation using hydroboranes or Cp2ZrHCl followed by transmetalation to afford organozinc reagents, which engage in catalyzed enantioselective additions to aldehydes: (a) Oppolzer, W, Radinov, R. Helv. Chim. Acta 1992, 75, 170
    • 2ZrHCl followed by transmetalation to afford organozinc reagents, which engage in catalyzed enantioselective additions to aldehydes: (a) Oppolzer, W.; Radinov, R. Helv. Chim. Acta 1992, 75, 170.
  • 51
    • 4544221552 scopus 로고    scopus 로고
    • For recent reviews on Brønsted acid organocatalysis, see: a
    • For recent reviews on Brønsted acid organocatalysis, see: (a) Pihko, P. M. Angew. Chem., Int. Ed. 2004, 43, 2062.
    • (2004) Angew. Chem., Int. Ed , vol.43 , pp. 2062
    • Pihko, P.M.1
  • 53
    • 0037178064 scopus 로고    scopus 로고
    • Hydrogenolysis of rhodium formate complexes has been postulated to occur through a six-centered transition structure. See: Musashi, Y, Sakaki, S. J. Am. Chem. Soc. 2002, 124, 7588
    • Hydrogenolysis of rhodium formate complexes has been postulated to occur through a six-centered transition structure. See: Musashi, Y.; Sakaki, S. J. Am. Chem. Soc. 2002, 124, 7588.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.