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Volumn 133, Issue 16, 2011, Pages 6126-6129

Convergent asymmetric disproportionation reactions: Metal/Brønsted acid relay catalysis for enantioselective reduction of quinoxalines

Author keywords

[No Author keywords available]

Indexed keywords

DISPROPORTIONATION REACTIONS; DISPROPORTIONATIONS; ENANTIOSELECTIVE REDUCTION; HYDRIDE TRANSFERS; HYDROGEN GAS; QUINOXALINES; REDUCTANTS;

EID: 79955041226     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja200723n     Document Type: Article
Times cited : (173)

References (73)
  • 5
    • 33745683617 scopus 로고    scopus 로고
    • For recent reviews of chiral phosphoric acids, see
    • For recent reviews of chiral phosphoric acids, see: Akiyama, T.; Itoh, J.; Fuchibe, K. Adv. Synth. Catal. 2006, 348, 999
    • (2006) Adv. Synth. Catal. , vol.348 , pp. 999
    • Akiyama, T.1    Itoh, J.2    Fuchibe, K.3
  • 12
    • 70349943846 scopus 로고    scopus 로고
    • For recent reviews of catalysts formed by combination of metals and chiral phosphoric acids, see
    • For recent reviews of catalysts formed by combination of metals and chiral phosphoric acids, see: Shao, Z. H.; Zhang, H. B. Chem. Soc. Rev. 2009, 38, 2745
    • (2009) Chem. Soc. Rev. , vol.38 , pp. 2745
    • Shao, Z.H.1    Zhang, H.B.2
  • 16
    • 33845961272 scopus 로고    scopus 로고
    • For asymmetric reactions catalyzed by metal/Brønsted acid relay catalysis systems, see
    • For asymmetric reactions catalyzed by metal/Brønsted acid relay catalysis systems, see: Komanduri, V.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 16448
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 16448
    • Komanduri, V.1    Krische, M.J.2
  • 27
    • 0035667895 scopus 로고    scopus 로고
    • For recent reviews of reversal of enantioselectivity in asymmetric reactions, see
    • For recent reviews of reversal of enantioselectivity in asymmetric reactions, see: Kim, Y. H. Acc. Chem. Res. 2001, 34, 955
    • (2001) Acc. Chem. Res. , vol.34 , pp. 955
    • Kim, Y.H.1
  • 32
    • 29144521717 scopus 로고    scopus 로고
    • For recent reviews of asymmetric hydrogenation of aromatic compounds, see
    • For recent reviews of asymmetric hydrogenation of aromatic compounds, see: Glorius, F. Org. Biomol. Chem. 2005, 3, 4171
    • (2005) Org. Biomol. Chem. , vol.3 , pp. 4171
    • Glorius, F.1
  • 36
    • 0003400749 scopus 로고
    • For asymmetric reduction of quinoxalines, see
    • For asymmetric reduction of quinoxalines, see: Murata, S.; Sugimoto, T.; Matsuura, S. Heterocycles 1987, 26, 763
    • (1987) Heterocycles , vol.26 , pp. 763
    • Murata, S.1    Sugimoto, T.2    Matsuura, S.3
  • 46
    • 0041825591 scopus 로고    scopus 로고
    • For asymmetric reduction of other heteroaromatic compounds, see: Quinolines
    • For asymmetric reduction of other heteroaromatic compounds, see: Quinolines: Wang, W. B.; Lu, S. M.; Yang, P. Y.; Han, X. W.; Zhou, Y. G. J. Am. Chem. Soc. 2003, 125, 10536
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 10536
    • Wang, W.B.1    Lu, S.M.2    Yang, P.Y.3    Han, X.W.4    Zhou, Y.G.5
  • 68
    • 35348853794 scopus 로고    scopus 로고
    • references cited therein
    • Connon, S. J. Org. Biomol. Chem. 2007, 5, 3407 and references cited therein.
    • (2007) Org. Biomol. Chem. , vol.5 , pp. 3407
    • Connon, S.J.1
  • 69
    • 79955025236 scopus 로고    scopus 로고
    • Low conversion (30%) and almost 0% ee were obtained when 3-phenyl-2 H -1,4-benzoxazine replaced 4b as the starting material in eq 10 in Scheme 4. When compounds 4a and 4b (1:1) were reacted in the same reaction vessel in benzene, the ee of 3a was 93% and compound 5 was obtained in 94% ee as a result of the hydride transfer from 4a to 4b in the presence of chiral phosphoric acid (S)- 1b. A mixture of 5 and 3a (1.00:0.64) suggested that the formation of 3a was not faster than that of 5
    • Low conversion (30%) and almost 0% ee were obtained when 3-phenyl-2 H -1,4-benzoxazine replaced 4b as the starting material in eq 10 in Scheme 4. When compounds 4a and 4b (1:1) were reacted in the same reaction vessel in benzene, the ee of 3a was 93% and compound 5 was obtained in 94% ee as a result of the hydride transfer from 4a to 4b in the presence of chiral phosphoric acid (S)- 1b. A mixture of 5 and 3a (1.00:0.64) suggested that the formation of 3a was not faster than that of 5.


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