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Volumn 9, Issue 26, 2007, Pages 5597-5599

Nickel-catalyzed enantio- and diastereoselective three-component coupling of 1,3-dienes, aldehydes, and silanes using chiral N-heterocyclic carbenes as ligands

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; HETEROCYCLIC COMPOUND; LIGAND; NICKEL; SILANE DERIVATIVE;

EID: 38349171275     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702543m     Document Type: Article
Times cited : (105)

References (40)
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    • (a) Zhu, J., Bienaymé, H., Eds. In Multicomponent Reactions; Wiley-VCH Verlag Gmbh and Co. KGaA: Weinhein, Germany, 2005.
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    • Reviews on Ni(0)-catalyzed multicomponent coupling, see: (a) Ikeda, S.-i
    • Reviews on Ni(0)-catalyzed multicomponent coupling, see: (a) Ikeda, S.-i. Acc. Chem. Res. 2000, 33, 511.
    • (2000) Acc. Chem. Res , vol.33 , pp. 511
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    • 3890. For recent examples of Ni(0)-catalyzed multicomponent coupling
    • (c) Montgomery, J. Angew. Chem., Int. Ed. 2004, 43, 3890. For recent examples of Ni(0)-catalyzed multicomponent coupling:
    • (2004) Angew. Chem., Int. Ed , vol.43
    • Montgomery, J.1
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    • Reviews of NHC ligands: (a) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290.
    • Reviews of NHC ligands: (a) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290.
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    • Nolan, S. P, Ed, Wiley-VCH Verlag Gmbh and Co. KGaA: Weinhein, Germany
    • (b) Nolan, S. P., Ed. In N-Heterocyclic Carbenes in Synthesis; Wiley-VCH Verlag Gmbh and Co. KGaA: Weinhein, Germany, 2006.
    • (2006) N-Heterocyclic Carbenes in Synthesis
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    • For NHC ligands for Ni complex, see
    • (c) For NHC ligands for Ni complex, see: Tekavec, T. N.; Louie, J. Top. Organomet. Chem. 2007, 21, 159.
    • (2007) Top. Organomet. Chem , vol.21 , pp. 159
    • Tekavec, T.N.1    Louie, J.2
  • 21
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    • Reviews of asymmetric reaction using chiral NHC ligands: (a) Gade, L. H.; Bellemin-Laponnaz, S. Top. Organomet. Chem. 2007, 21, 117.
    • Reviews of asymmetric reaction using chiral NHC ligands: (a) Gade, L. H.; Bellemin-Laponnaz, S. Top. Organomet. Chem. 2007, 21, 117.
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    • Perry, M. C.; Burgess, K. Tetrahedron: Asymmetry 2003, 14, 951. For representative examples of asymmetric C-C bond forming reaction catalyzed by metal-NHC* complex, see:
    • (b) Perry, M. C.; Burgess, K. Tetrahedron: Asymmetry 2003, 14, 951. For representative examples of asymmetric C-C bond forming reaction catalyzed by metal-NHC* complex, see:
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    • Martin, D.; Kehrli, S.; d'Augustin, M.; Clavier, H.; Mauduit, M.; Alexakis, A. J. Am. Chem. Soc. 2006, 128, 8416. Very recently, a Ni(0)-catalyzed asymmetric coupling using a chiral NHC ligand has been reported, see:
    • (j) Martin, D.; Kehrli, S.; d'Augustin, M.; Clavier, H.; Mauduit, M.; Alexakis, A. J. Am. Chem. Soc. 2006, 128, 8416. Very recently, a Ni(0)-catalyzed asymmetric coupling using a chiral NHC ligand has been reported, see:
  • 32
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    • For other examples of Ni(0)-catalyzed asymmetric coupling, see:(a) Ikeda, S.-i.; Cui, D.-M.; Sato, Y. J. Am. Chem. Soc. 1999, 121, 4712.
    • For other examples of Ni(0)-catalyzed asymmetric coupling, see:(a) Ikeda, S.-i.; Cui, D.-M.; Sato, Y. J. Am. Chem. Soc. 1999, 121, 4712.
  • 38
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    • iPr as a ligand under similar conditions also gave 1cc (95%, anti:syn = 11:1) or 1dc (58%, anti only) in a diastereoselective manner: Sawaki, R.; Mori, M.; Sato, Y. Unpublished results.
    • iPr as a ligand under similar conditions also gave 1cc (95%, anti:syn = 11:1) or 1dc (58%, anti only) in a diastereoselective manner: Sawaki, R.; Mori, M.; Sato, Y. Unpublished results.
  • 39
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    • 2 using chiral phosphoramidite ligands has been reported. See: Yang, Y.; Zhu, S.-F.; Duan, H.-F.; Zhou, C.-Y.; Wang, L.-X.; Zhou, Q.-L. J. Am. Chem. Soc. 2007, 129, 2248.
    • 2 using chiral phosphoramidite ligands has been reported. See: Yang, Y.; Zhu, S.-F.; Duan, H.-F.; Zhou, C.-Y.; Wang, L.-X.; Zhou, Q.-L. J. Am. Chem. Soc. 2007, 129, 2248.
  • 40
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    • For determination of the absolute and relative configuration of the coupling products, see Supporting Information
    • For determination of the absolute and relative configuration of the coupling products, see Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.