A Dienyl Boronate-Aryl Nitroso Ene Reaction Entry to C-Pyrrolyl Nitrones and Subsequent Conversion to Isoxazolidines

Abstract : A new cascade reaction to access C-pyrrolyl nitrones en route to isoxazolidines is reported; a process that involves four successive steps, the first key step being an ene-reaction of a 3-methyl-1,3-dienylboronate ester with an aryl nitroso compounds to derive uncommon 1,3-dipoles which react with various alkenes to access isoxazolidines. The scope and mechanism of the cascade sequence is discussed.
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Submitted on : Monday, June 4, 2018 - 2:00:11 PM
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Ludovic Eberlin, Aurélie Macé, Andrei S. Batsanov, Bertrand Carboni, Andrew Whiting. A Dienyl Boronate-Aryl Nitroso Ene Reaction Entry to C-Pyrrolyl Nitrones and Subsequent Conversion to Isoxazolidines. ChemistrySelect, Wiley, 2018, 3 (16), pp.4557-4561. ⟨10.1002/slct.201800945⟩. ⟨hal-01807080⟩

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