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Volumn 8, Issue 26, 2006, Pages 6059-6062

A three-component tandem reductive aldol reaction catalyzed by N-heterocyclic carbene-copper complexes

Author keywords

[No Author keywords available]

Indexed keywords

CARBENE; COPPER; DRUG DERIVATIVE; HETEROCYCLIC COMPOUND; HYDROCARBON; METHANE;

EID: 33846176873     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062495o     Document Type: Article
Times cited : (84)

References (30)
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    • Selected examples in catalysis: Allylic alkylation: (a) Tominaga, S.; Oi, Y.; Kato, T.; Keun, An D.; Okamoto, S. Tetrahedron Lett. 2004, 45, 5585-5588.
    • Selected examples in catalysis: Allylic alkylation: (a) Tominaga, S.; Oi, Y.; Kato, T.; Keun, An D.; Okamoto, S. Tetrahedron Lett. 2004, 45, 5585-5588.
  • 4
    • 0035968410 scopus 로고    scopus 로고
    • Asymmetric conjugated addition of organometallics to enones: (c) Guillen, F.; Winn, C. L.; Alexakis, A. Tetrahedron: Asymmetry 2001, 12, 2083-2086.
    • Asymmetric conjugated addition of organometallics to enones: (c) Guillen, F.; Winn, C. L.; Alexakis, A. Tetrahedron: Asymmetry 2001, 12, 2083-2086.
  • 9
    • 4444313323 scopus 로고    scopus 로고
    • Carbene transfer: (h) Fructos, M. R.; Belderrain, T. R.; Nicasio, M. C.; Nolan, S. P.; Kaur, H.; Diaz-Requejo, M. M.; Pérez, P. J. J. Am. Chem. Soc. 2004, 126, 10846-10847.
    • Carbene transfer: (h) Fructos, M. R.; Belderrain, T. R.; Nicasio, M. C.; Nolan, S. P.; Kaur, H.; Diaz-Requejo, M. M.; Pérez, P. J. J. Am. Chem. Soc. 2004, 126, 10846-10847.
  • 10
    • 33744502921 scopus 로고    scopus 로고
    • Boration of alkenes and aldehydes (i) Laitar, D. S.; Tsui, E. Y.; Sadighi, J. P. Organometallics 2006, 25, 2405-2408.
    • Boration of alkenes and aldehydes (i) Laitar, D. S.; Tsui, E. Y.; Sadighi, J. P. Organometallics 2006, 25, 2405-2408.
  • 19
    • 0032506682 scopus 로고    scopus 로고
    • For intramolecular reductive aldol reaction with a stoichiometric amount of Stryker's reagent, see: a
    • For intramolecular reductive aldol reaction with a stoichiometric amount of Stryker's reagent, see: (a) Chiu, P.; Chen, B.; Cheng, K. F. Tetrahedron Lett. 1998, 39, 9229-9232.
    • (1998) Tetrahedron Lett , vol.39 , pp. 9229-9232
    • Chiu, P.1    Chen, B.2    Cheng, K.F.3
  • 22
    • 9144228846 scopus 로고    scopus 로고
    • For intramolecular reductive aldol reaction with a catalytic amount of Stryker's reagent, see: d
    • For intramolecular reductive aldol reaction with a catalytic amount of Stryker's reagent, see: (d) Chiu, P.; Leung, S. K. Chem. Commun. 2004, 2308-2309.
    • (2004) Chem. Commun , pp. 2308-2309
    • Chiu, P.1    Leung, S.K.2
  • 23
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    • (e) Chiu. P. Synthesis 2004, 2210-2215.
    • (2004) Synthesis , pp. 2210-2215
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  • 24
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    • 2O, see : (f) Lam, H. W.; Joensuu, P. M. Org. Lett. 2005, 7, 4225-4228.
    • 2O, see : (f) Lam, H. W.; Joensuu, P. M. Org. Lett. 2005, 7, 4225-4228.
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    • 3SiH, 180 euros/mol.
    • 3SiH, 180 euros/mol.
  • 30
    • 33846143630 scopus 로고    scopus 로고
    • Typical Procedure for Tandem Hydrosilylation-Aldolization. A flame-dried flask under argon was loaded with the (NHC)copper complex (0.01 mmol, 0.01 equiv) under argon. A 5 mL portion of freshly distilled toluene was introduced, followed by sequential addition of the electrophilic olefin (1.1 mmol, 1.1 equiv), the electrophile (1 mmol, 1 equiv), and the silane (1.2 mmol, 1.2 equiv). After being stirred for 1 h, the solution was stirred for an additional 1 h under air. The volatile compounds were removed under reduced pressure, and the residue was purified by chromatography on triethylamine- pacified silica gel.
    • Typical Procedure for Tandem Hydrosilylation-Aldolization. A flame-dried flask under argon was loaded with the (NHC)copper complex (0.01 mmol, 0.01 equiv) under argon. A 5 mL portion of freshly distilled toluene was introduced, followed by sequential addition of the electrophilic olefin (1.1 mmol, 1.1 equiv), the electrophile (1 mmol, 1 equiv), and the silane (1.2 mmol, 1.2 equiv). After being stirred for 1 h, the solution was stirred for an additional 1 h under air. The volatile compounds were removed under reduced pressure, and the residue was purified by chromatography on triethylamine- pacified silica gel.


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