Bestmann’s ylide, Ph3P=C=C=O, has been widely used as chemical linchpin reagent in synthesis of natural products and was found to undergo various [2+2], [2+3] and [2+4] cycloaddition reactions. Here we investigated the activity of several boron containing Lewis acids as a catalyst for the [2+3] cycloaddition reactions of Ph3P=C=C=O with various nitrones to give the corresponding 5- isoxazolidinone substituited triphenylphosphonium ylides. These new ylides can serve as precursors in Wittig reactions to form biologically important heterocyclic compounds, which can be hydrogenated to generate β-amino acids. The substrate scope and mechanistic aspects of the reaction will be discussed.

BPh3 catalyzed [2+3] cycloaddition of Ph3P=C=C=O with nitrones to 4-triphenylphosphoranylidene-5-isoxazolidinones

2019 Fall National Meeting

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