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Highly Diastereoselective Iron-Mediated C(sp2)[BOND]C(sp3) Cross-Coupling Reactions between Aryl Grignard Reagents and Cyclic Iodohydrine Derivatives

Authors

  • Andreas K. Steib,

    1. Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5–13, Haus F, 81377 München (Germany), Fax: (+49) 89-2180-77680
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    • These authors contributed equally to this work.

  • Tobias Thaler,

    1. Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5–13, Haus F, 81377 München (Germany), Fax: (+49) 89-2180-77680
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    • These authors contributed equally to this work.

  • Prof. Dr. Kimihiro Komeyama,

    1. Department of Chemistry and Chemical Engineering, Graduate School of Engineering, Hiroshima University, Kagamiyama, Higashi-Hiroshima 739-8527 (Japan)
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  • Dr. Peter Mayer,

    1. Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5–13, Haus F, 81377 München (Germany), Fax: (+49) 89-2180-77680
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  • Prof. Dr. Paul Knochel

    Corresponding author
    1. Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5–13, Haus F, 81377 München (Germany), Fax: (+49) 89-2180-77680
    • Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5–13, Haus F, 81377 München (Germany), Fax: (+49) 89-2180-77680
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  • Funding from the European Research Council under the European Community’s Seventh Framework Programme (FP7/2007-2013, ERC grant no. 227763) is acknowledged. We thank the SFB 749 and the Fonds der Chemischen Industrie for financial support, and are grateful to BASF AG, W. C. Heraeus GmbH, Chemetall GmbH, and Solvias AG for the generous gift of chemicals. K.K. thanks the Japan Society for the Promotion of Sciences (JSPS) for financial support.

Abstract

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trans-2-Arylcycloalcohol derivatives are obtained in high diastereoselectivity by the iron-mediated cross-coupling of cyclic TBS-protected iodohydrines with aryl Grignard reagents (see scheme; TBS=tert-butyldimethylsilyl). The stereoconvergent cross-coupling of a chiral TBS-protected 2-iodocyclohexanol provides the 2-arylcyclohexanols with no loss of stereochemical purity, and is a valuable alternative to the enantioselective opening of symmetrical epoxides.

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