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Volumn , Issue 24, 2013, Pages 5398-5413

C-5′-substituted cinchona alkaloid derivatives catalyse the first highly enantioselective dynamic kinetic resolutions of azlactones by thiolysis

Author keywords

Heterocycles; Kinetic resolution; Organocatalysis; Peptides; Synthetic methods

Indexed keywords


EID: 84881664163     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201300451     Document Type: Article
Times cited : (26)

References (79)
  • 3
    • 84859581750 scopus 로고    scopus 로고
    • For a recent review of the organocatalytic DKR of azlactones, see
    • For a recent review of the organocatalytic DKR of azlactones, see:, Z. Rodriguez-Docampo, S. J. Connon, ChemCatChem 2012, 4, 151.
    • (2012) ChemCatChem , vol.4 , pp. 151
    • Rodriguez-Docampo, Z.1    Connon, S.J.2
  • 5
    • 28244495310 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 3974
    • E. Vedejs, M. Jure, Angew. Chem. 2005, 117, 4040; Angew. Chem. Int. Ed. 2005, 44, 3974.
    • (2005) Angew. Chem. , vol.117 , pp. 4040
    • Vedejs, E.1    Jure, M.2
  • 31
    • 34247532540 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 7668
    • D. Macmillan, Angew. Chem. 2006, 118, 7830; Angew. Chem. Int. Ed. 2006, 45, 7668.
    • (2006) Angew. Chem. , vol.118 , pp. 7830
    • Macmillan, D.1
  • 36
    • 79961227451 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2010, 49, 9500
    • Z. Tan, S. Shang, S. J. Danishefsky, Angew. Chem. 2010, 122, 9690; Angew. Chem. Int. Ed. 2010, 49, 9500.
    • (2010) Angew. Chem. , vol.122 , pp. 9690
    • Tan, Z.1    Shang, S.2    Danishefsky, S.J.3
  • 39
    • 79961236497 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2011, 50, 1232
    • F. Mende, O. Seitz, Angew. Chem. 2011, 123, 1266; Angew. Chem. Int. Ed. 2011, 50, 1232.
    • (2011) Angew. Chem. , vol.123 , pp. 1266
    • Mende, F.1    Seitz, O.2
  • 57
    • 33746322013 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 1520
    • M. S. Taylor, E. N. Jacobsen, Angew. Chem. 2006, 118, 1550; Angew. Chem. Int. Ed. 2006, 45, 1520.
    • (2006) Angew. Chem. , vol.118 , pp. 1550
    • Taylor, M.S.1    Jacobsen, E.N.2
  • 60
    • 34347258004 scopus 로고    scopus 로고
    • For a review of the application of cupreine/cupreidines as catalysts, see:, Angew. Chem. Int. Ed. 2006, 45, 7496
    • For a review of the application of cupreine/cupreidines as catalysts, see:, T. Marcelli, J. H. van Maarseveen, H. Hiemstra, Angew. Chem. 2006, 118, 7658; Angew. Chem. Int. Ed. 2006, 45, 7496.
    • (2006) Angew. Chem. , vol.118 , pp. 7658
    • Marcelli, T.1    Van Maarseveen, J.H.2    Hiemstra, H.3
  • 68
    • 0033520752 scopus 로고    scopus 로고
    • For the first use of this material as an asymmetric organocatalyst, see
    • For the first use of this material as an asymmetric organocatalyst, see:, Y. Iwabuchi, M. Nakatani, N. Yokoyama, S. Hatakeyama, J. Am. Chem. Soc. 1999, 121, 10219.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 10219
    • Iwabuchi, Y.1    Nakatani, M.2    Yokoyama, N.3    Hatakeyama, S.4
  • 79
    • 28944433821 scopus 로고    scopus 로고
    • 2O) contains a bound water molecule in its crystalline form. Thus it is tempting (by analogy) to suggest that 26 (which is also a demethylated cinchona alkaloid) may be particularly hygroscopic, which would in part, explain the high propensity for hydrolysis despite considerable precautions to avoid the introduction of moisture into the system. See
    • 2O) contains a bound water molecule in its crystalline form. Thus it is tempting (by analogy) to suggest that 26 (which is also a demethylated cinchona alkaloid) may be particularly hygroscopic, which would in part, explain the high propensity for hydrolysis despite considerable precautions to avoid the introduction of moisture into the system. See:, A. Nakano, S. Kawahara, S. Akamatsu, K. Morokuma, M. Nakatani, Y. Iwabuchi, K. Takahashi, J. Ishihar, S. Hatakeyama, Tetrahedron 2006, 62, 381.
    • (2006) Tetrahedron , vol.62 , pp. 381
    • Nakano, A.1    Kawahara, S.2    Akamatsu, S.3    Morokuma, K.4    Nakatani, M.5    Iwabuchi, Y.6    Takahashi, K.7    Ishihar, J.8    Hatakeyama, S.9


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.