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Gold‐Catalyzed Formal 1,6‐Acyloxy Migration Leading to 3,4‐Disubstituted Pyrrolidin‐2‐ones
Author(s) -
Hashmi A. Stephen K.,
Yang Weibo,
Yu Yang,
Hansmann Max M.,
Rudolph Matthias,
Rominger Frank
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201207287
Subject(s) - chemistry , computer science , tandem , combinatorial chemistry , stereochemistry , transformation (genetics) , biochemistry , engineering , gene , aerospace engineering
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.