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Volumn 131, Issue 11, 2009, Pages 3858-3859

Two methods for catalytic generation of reactive enolates promoted by a chiral poly Gd complex: Application to catalytic enantioselective protonation reactions

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; CYANIDES; ENANTIOSELECTIVITY; ETHERS; ORGANIC COMPOUNDS; PROTONATION; PROTONS; SILANES;

EID: 67749110131     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9005018     Document Type: Article
Times cited : (50)

References (33)
  • 7
    • 0030724513 scopus 로고    scopus 로고
    • For reviews of enantioselective protonation of prochiral metal enolates, see
    • (g) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366. For reviews of enantioselective protonation of prochiral metal enolates, see:
    • (1997) Angew. Chem., Int. Ed. Engl , vol.36 , pp. 2366
    • Sugiura, M.1    Nakai, T.2
  • 11
    • 84924187517 scopus 로고    scopus 로고
    • See Supporting Information for details
    • See Supporting Information for details.
  • 12
    • 84924100157 scopus 로고    scopus 로고
    • Ligand 1, which provides a completely different higher-order structure (2:3 and/or 4:5 complex), and ligand 4, which provides a 5:6 complex but contains a more electron-rich catechol (thus, containing a less acidic proton in the catalyst), produced strikingly reduced enantioselectivity (less than 42% ee).
    • Ligand 1, which provides a completely different higher-order structure (2:3 and/or 4:5 complex), and ligand 4, which provides a 5:6 complex but contains a more electron-rich catechol (thus, containing a less acidic proton in the catalyst), produced strikingly reduced enantioselectivity (less than 42% ee).
  • 13
    • 57549091031 scopus 로고    scopus 로고
    • For examples of catalytic sequential conjugate addition-enantioselective protonation, see: (a) Sibi, M. P, Coulomb, J, Stanley, L. M. Angew. Chem, Int. Ed. 2008, 47, 9913
    • For examples of catalytic sequential conjugate addition-enantioselective protonation, see: (a) Sibi, M. P.; Coulomb, J.; Stanley, L. M. Angew. Chem., Int. Ed. 2008, 47, 9913.
  • 25
    • 34248684099 scopus 로고    scopus 로고
    • For a catalytic enantioselective conjugate cyanation of β-substituted, α-unsubstituted VV-acyl pyrroles catalyzed by a Gd complex derived from 2, see: Fujimori, I.; Mita, T.; Maki, K.; Shiro, M.; Sato, A.; Furusho, S.; Kanai, M.; Shibasaki, M. Tetrahedron 2007, 63, 5820.
    • For a catalytic enantioselective conjugate cyanation of β-substituted, α-unsubstituted VV-acyl pyrroles catalyzed by a Gd complex derived from 2, see: Fujimori, I.; Mita, T.; Maki, K.; Shiro, M.; Sato, A.; Furusho, S.; Kanai, M.; Shibasaki, M. Tetrahedron 2007, 63, 5820.
  • 28
    • 84924176598 scopus 로고    scopus 로고
    • The use of DMP as a proton source afforded less satisfactory enantiose- lectivity, and ligand 3 demonstrated no significant advantage compared to 2. The reaction rate and enantioselectivity were much lower when using a catalytic amount of TMSCN (10 mol %)and 1 equiv of HCN (11:90h, 61% yield, 50% ee; cf. Table 2, entry 1).
    • The use of DMP as a proton source afforded less satisfactory enantiose- lectivity, and ligand 3 demonstrated no significant advantage compared to 2. The reaction rate and enantioselectivity were much lower when using a catalytic amount of TMSCN (10 mol %)and 1 equiv of HCN (11:90h, 61% yield, 50% ee; cf. Table 2, entry 1).
  • 29
    • 41449104100 scopus 로고    scopus 로고
    • A catalytic asymmetric cross-coupling reaction to generate carboxylic acid derivatives containing a-aryl-substituted tertiary stereocenters: Dai, X, Strotman, N. A, Fu, G. C. J. Am. Chem. Soc. 2008, 130, 3302
    • (a) A catalytic asymmetric cross-coupling reaction to generate carboxylic acid derivatives containing a-aryl-substituted tertiary stereocenters: Dai, X.; Strotman, N. A.; Fu, G. C. J. Am. Chem. Soc. 2008, 130, 3302.
  • 30
    • 0034607295 scopus 로고    scopus 로고
    • Organocatalyzed redox alkylation and arylation of aldehydes
    • (b) Davies, H. M. L.; Hansen, T.; Churchill, M. R. J. Am. Chem. Soc. 2000, 122, 3063. Organocatalyzed redox alkylation and arylation of aldehydes:
    • (2000) J. Am. Chem. Soc , vol.122 , pp. 3063
    • Davies, H.M.L.1    Hansen, T.2    Churchill, M.R.3
  • 33
    • 84924092456 scopus 로고    scopus 로고
    • Based on the absolute configuration of 11, the geometry of the reactive intermediate enolate 7 generated via conjugate cyanation would be E (when the priority of R is higher than the cyanomethyl group).
    • Based on the absolute configuration of 11, the geometry of the reactive intermediate enolate 7 generated via conjugate cyanation would be E (when the priority of R is higher than the cyanomethyl group).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.