Highly Stereoselective Ring Expansion Reactions Mediated by Attractive Cation–n Interactions

Authors

  • Timothy Ribelin,

    1. Department of Medicinal Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Malott Hall, Room 4070, Lawrence, KS 66047 (USA), Fax: (+1) 785-864-5326
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  • Christopher E. Katz Dr.,

    1. Department of Medicinal Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Malott Hall, Room 4070, Lawrence, KS 66047 (USA), Fax: (+1) 785-864-5326
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  • Donna G. English,

    1. Department of Chemistry and Biochemistry, Old Dominion University, 4541 Hampton Boulevard, Norfolk, Virginia 23529 (USA), Fax: (+1) 757-683-4628
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  • Sherriel Smith,

    1. Department of Chemistry and Biochemistry, Old Dominion University, 4541 Hampton Boulevard, Norfolk, Virginia 23529 (USA), Fax: (+1) 757-683-4628
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  • Anna K. Manukyan,

    1. Department of Chemistry and Biochemistry, Old Dominion University, 4541 Hampton Boulevard, Norfolk, Virginia 23529 (USA), Fax: (+1) 757-683-4628
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  • Victor W. Day Dr.,

    1. Department of Medicinal Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Malott Hall, Room 4070, Lawrence, KS 66047 (USA), Fax: (+1) 785-864-5326
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  • Benjamin Neuenswander,

    1. Department of Medicinal Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Malott Hall, Room 4070, Lawrence, KS 66047 (USA), Fax: (+1) 785-864-5326
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  • Jennifer L. Poutsma Prof.,

    1. Department of Chemistry and Biochemistry, Old Dominion University, 4541 Hampton Boulevard, Norfolk, Virginia 23529 (USA), Fax: (+1) 757-683-4628
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  • Jeffrey Aubé Prof.

    1. Department of Medicinal Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Malott Hall, Room 4070, Lawrence, KS 66047 (USA), Fax: (+1) 785-864-5326
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  • Financial support of this work by the Institute of General Medical Sciences (NIH) is gratefully acknowledged (GM 49093, J.A.). Acknowledgement is made to the donors of the American Chemical Society Petroleum Research Fund for partial support of this research (to J.L.P.). We also thank Prof. Paul Hanson and his group for their gas chromatograph. n=nonbonded electrons.

Abstract

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Im Griff: Eine anziehende elektrostatische Kraft stabilisiert die Konformation einer Zwischenstufe (siehe Schema; n=nichtgebundenes Elektron) und legt so die Konfiguration der Abgangsgruppe fest, was in einer asymmetrischen Ringerweiterungsreaktion zu einer außergewöhnlich hohen Diastereoselektivität führt.

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