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Gold-catalyzed formal 1,6-acyloxy migration leading to 3,4-disubstituted pyrrolidin-2-ones

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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,...

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Bibliographic Details
Main Authors: Hashmi, A. Stephen K. (Author) , Yang, Weibo (Author) , Yu, Yang (Author) , Hansmann, Max M. (Author) , Rudolph, Matthias (Author) , Rominger, Frank (Author)
Format: Article (Journal)
Language:English
Published: 2013
In: Angewandte Chemie. International edition
Year: 2012, Volume: 52, Issue: 4, Pages: 1329-1332
ISSN:1521-3773
DOI:10.1002/anie.201207287
Online Access:Verlag, Volltext: http://dx.doi.org/10.1002/anie.201207287
Verlag, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201207287
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Author Notes:A. Stephen K. Hashmi, Weibo Yang, Yang Yu, Max M. Hansmann, Matthias Rudolph, and Frank Rominger
Description
Summary: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.
Item Description:Gesehen am 04.09.2018
First published: 04 December 2012
Physical Description:Online Resource
ISSN:1521-3773
DOI:10.1002/anie.201207287

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