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Electrophile-Induced Ether Transfer: Stereoselective Synthesis of 2,4,6-Trisubstituted Tetrahydropyrans

Authors

  • Rendy Kartika,

    1. Department of Chemistry and Biochemistry and the Walther Cancer Research Center, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, IN 46556-5670, USA, Fax: (+1) 574-631-5674
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  • Richard E. Taylor Prof.

    1. Department of Chemistry and Biochemistry and the Walther Cancer Research Center, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, IN 46556-5670, USA, Fax: (+1) 574-631-5674
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  • Support provided by the National Institutes of Health through the National Institute of General Medical Science (GM007683) is gratefully acknowledged.

Abstract

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Ein negativer Angriff: Die Synthese von 4-Alkoxy-2,6-cis- und seinem stereokomplementären 4-Alkoxy-2,6-trans-tetrahydropyran gelang in hoher Ausbeute und mit hervorragender Stereokontrolle mithilfe der gleichen Strategie: durch ein Elektrophil induzierter Ethertransfer, Cyclisierung und Funktionalisierungsreaktionen (siehe Schema; Bn=Benzyl, BPS=tBuPh2Si, TEA=Et3N, TBS=tBuMe2Si).

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