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Gold-Catalyzed Formal 1,6-Acyloxy Migration Leading to 3,4-Disubstituted Pyrrolidin-2-ones

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  • W.Y. and Y.Y. are grateful to the CSC for a fellowship. M.M.H. thanks the Fonds der chemischen Industrie for a Chemiefonds scholarship and the Studienstiftung des deutschen Volkes. Gold salts were generously donated by Umicore AG & Co. KG. The computational studies were supported by bwGRiD, member of the German D-Grid initiative, funded by the Ministry for Education and Research and the Ministry for Science, Research and Arts Baden-Württemberg.

Abstract

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Mobile: The title reaction affords diastereomerically pure 3,4-disubstituted pyrrolidin-2-ones, which are important structural motifs in natural products, in good to high yields. Mechanistic investigations suggest the transformation proceeds through a tandem 1,3-acyloxy migration and a subsequent 1,5-acyloxy migration. DCE=1,2-dichloroethane, IPr=1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene.

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