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Nucleophilic Addition to N-Phosphinylimines by Rare-Earth-Metal Triflate/Trifluoroacetic Anhydride Activation

Authors

  • Winnie W. Ong,

    1. Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, MA 02215, USA, Fax: (+1) 617-358-2847
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  • Aaron B. Beeler Dr.,

    1. Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, MA 02215, USA, Fax: (+1) 617-358-2847
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  • Sarathy Kesavan Dr.,

    1. Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, MA 02215, USA, Fax: (+1) 617-358-2847
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  • James S. Panek Prof. Dr.,

    1. Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, MA 02215, USA, Fax: (+1) 617-358-2847
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  • John A. Porco Jr. Prof. Dr.

    1. Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, MA 02215, USA, Fax: (+1) 617-358-2847
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  • This work was generously supported by the NIGMS CMLD initiative (P50 GM067041). We thank Professors Scott Schaus (Boston University) and Jinquan Yu (Brandeis University) for helpful discussions, Dr. Paul Ralifo (Boston University) for assistance with NMR structure elucidation, CEM Corporation (Matthews, NC) for assistance with microwave instrumentation, and Symyx Technologies, Inc. (Santa Clara, CA) for assistance with chemical reaction planning software.

Abstract

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Hydratisiertes Lanthantriflat ist ein effizienter und hoch aktiver Lewis-Säure-Katalysator für die Addition eines Nucleophils an N-Phosphinylimine in Gegenwart von Trifluoressigsäureanhydrid (TFAA; siehe Schema). Vermutlich durch eine Folge aus Acylierung und Hydratisierung des N-Phosphinylimins mit anschließender nucleophiler Addition werden in einer neuartigen Umwandlung Trifluoracetamide produziert.

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