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Enantio- and Diastereoselective Hydrogenation of Farnesol and O-Protected Derivatives: Stereocontrol by Changing the C[DOUBLE BOND]C Bond Configuration

Authors

  • Aie Wang Dr.,

    1. Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel, Switzerland, Fax: (+41) 61-267-1103
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  • Bettina Wüstenberg Dr.,

    1. Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel, Switzerland, Fax: (+41) 61-267-1103
    2. Current address: Research Center Chemical Process Technology, DSM Nutritional Products, P.O. Box 3255, 4002 Basel, Switzerland
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  • Andreas Pfaltz Prof. Dr.

    1. Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel, Switzerland, Fax: (+41) 61-267-1103
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  • Financial support from the Swiss National Science Foundation, the Federal Commission for Technology and Innovation (KTI), and Novartis Pharma (Fellowship Award to A.W.) is gratefully acknowledged. We thank Dr. Thomas Netscher (DSM Nutritional Products) for helpful discussions and a gift of farnesol.

Abstract

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Vier Isomere – ein Katalysator: Alle vier Stereoisomere von Hexahydrofarnesol sind hoch enantio- und diastereoselektiv mit dem chiralen Iridiumkatalysator 1 zugänglich, wenn man von unterschiedlichen cis/trans-Isomeren von Farnesol ausgeht (siehe Schema; BArF = Tetrakis[bis-3,5-(trifluormethyl)phenyl]borat). Sowohl die interne trialkylsubstituierte C[DOUBLE BOND]C-Bindung als auch die Allylalkohol-Einheit werden mit hoher Seitenselektivität hydriert.

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