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Volumn 51, Issue 4, 2012, Pages 971-974

Dioxindole in asymmetric catalytic synthesis: Routes to enantioenriched 3-substituted 3-hydroxyoxindoles and the preparation of maremycin A

Author keywords

asymmetric synthesis; molecular complexity; organocatalysis; oxindoles; spiro compounds

Indexed keywords

ASYMMETRIC SYNTHESIS; MOLECULAR COMPLEXITY; ORGANOCATALYSIS; OXINDOLES; SPIRO COMPOUNDS;

EID: 84855993419     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201107443     Document Type: Article
Times cited : (193)

References (56)
  • 6
    • 84873062777 scopus 로고    scopus 로고
    • K. Shen, X. Liu, L. Lin, X. Feng, Chem. Sci. 2011, DOI
    • K. Shen, X. Liu, L. Lin, X. Feng, Chem. Sci. 2011, DOI
  • 12
    • 74849131136 scopus 로고    scopus 로고
    • For selected examples using organocatalysis, see
    • Angew. Chem. Int. Ed. 2010, 49, 744. For selected examples using organocatalysis, see
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 744
  • 30
    • 4344664521 scopus 로고
    • Interestingly, when the authors tried to directly use dioxindole 1 in the Michael addition under strongly basic conditions, they obtained "deeply colored mixtures and â∥ï intractable tars", see
    • P. L. Julian, E. E. Dailey, H. C. Printy, H. L. Cohen, S. Hamashige, J. Am. Chem. Soc. 1956, 78, 3503. Interestingly, when the authors tried to directly use dioxindole 1 in the Michael addition under strongly basic conditions, they obtained "deeply colored mixtures and â∥ï intractable tars", see
    • (1956) J. Am. Chem. Soc. , vol.78 , pp. 3503
    • Julian, P.L.1    Dailey, E.E.2    Printy, H.C.3    Cohen, H.L.4    Hamashige, S.5
  • 35
    • 0001622458 scopus 로고
    • The radical intermediate II in Figure 2 is stabilized by a captodative effect, see
    • E. Ziegler, T. Kappe, R. Salvador, Monatsh. Chem. 1963, 94, 453. The radical intermediate II in Figure 2 is stabilized by a captodative effect, see
    • (1963) Monatsh. Chem. , vol.94 , pp. 453
    • Ziegler, E.1    Kappe, T.2    Salvador, R.3
  • 37
    • 33845377664 scopus 로고
    • Further details about the oxidative pathway that leads to isatide are discussed in Figure S3 in the Supporting Information. For a leading reference on the enolate oxidative coupling, see
    • H. G. Viehe, Z. Janousek, R. Merenyi, L. Stella, Acc. Chem. Res. 1985, 18, 148. Further details about the oxidative pathway that leads to isatide are discussed in Figure S3 in the Supporting Information. For a leading reference on the enolate oxidative coupling, see
    • (1985) Acc. Chem. Res. , vol.18 , pp. 148
    • Viehe, H.G.1    Janousek, Z.2    Merenyi, R.3    Stella, L.4
  • 42
    • 22144459070 scopus 로고    scopus 로고
    • For a recent review, see
    • Angew. Chem. Int. Ed. 2005, 44, 4212. For a recent review, see
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 4212
  • 48
    • 2542446237 scopus 로고    scopus 로고
    • Both a tertiary amine and an acid are able to reduce the optical purity of enantioenriched dioxindole 1 by promoting keto-enol tautomerization, see.
    • Both a tertiary amine and an acid are able to reduce the optical purity of enantioenriched dioxindole 1 by promoting keto-enol tautomerization, see:, O. J. Sonderegger, T. Bürgi, L. K. Limbach, A. Baiker, J. Mol. Catal. A 2004, 217, 93.
    • (2004) J. Mol. Catal. A , vol.217 , pp. 93
    • Sonderegger, O.J.1    Bürgi, T.2    Limbach, L.K.3    Baiker, A.4
  • 55
    • 70349693959 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 7911-7914
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 7911-7914


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.