Gold(I)‐Catalyzed N‐Desulfonylative Amination versus N‐to‐O 1,5‐Sulfonyl Migration: A Versatile Approach to 1‐Azabicycloalkanes |
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Authors: | Solène Miaskiewicz Boris Gaillard Dr Nicolas Kern Prof?Dr Jean‐Marc Weibel Prof?Dr Patrick Pale Dr Aurélien Blanc |
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Institution: | Laboratoire de Synthèse, Réactivité Organiques et Catalyse, UMR 7177 associé au CNRS, Institut de Chimie, Université de Strasbourg, Strasbourg, France |
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Abstract: | Valuable 1‐azabicycloalkane derivatives have been synthesized through a novel gold(I)‐catalyzed desulfonylative cyclization strategy. An ammoniumation reaction of ynones substituted at the 1‐position with an N‐sulfonyl azacycle took place in the presence of a gold cation by intramolecular cyclization of the disubstituted sulfonamide moiety onto the triple bond. Depending on the size of the heterocyclic ring and substitution of the substrates, two unprecedented forms of nucleophilic attack on the sulfonyl group were exploited, that is, a N‐desulfonylation in the presence of an external protic O nucleophile (37–87 %, 10 examples) and a unique N‐to‐O 1,5‐sulfonyl migration (60–98 %, 9 examples). |
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Keywords: | desulfonylation gold homogeneous catalysis N heterocycles sulfonyl migration |
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