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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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Gaining control: An attractive electrostatic force stabilizes the conformation of an intermediate (see scheme; n=nonbonded electron), thus controlling the leaving group configuration to give superior diastereoselectivity in an asymmetric ring expansion.

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