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Enantioconvergent and Diastereoselective Three-Component Linear Reactions Enabled by Gold and Oxidative
Xia Wang1, Shifei Liu1, Hao An1
1Frontiers Science Center for Flexible Electronics (FSCFE), Shaanxi Institute of Flexible Electronics (SIFE), and Shaanxi Institute of Biomedical Materials and Engineering (SIBME), Northwestern Polytechnical University (NPU), 127 West Youyi Road, Xi'an 710072, China.
Abstract:
An asymmetric relay catalysis strategy merging gold and oxidative N-heterocyclic carbenes (NHCs) for trimolecular reactions was disclosed. Racemic α-amino-ynones undergo facile conversion to racemic pyrrolin-3-ones under gold catalysis, which serve as potent nucleophilic C1 synthons, which engage easily available enals and phenols to generate linear products in moderate yields and excellent diastereo- and enantioselectivities under oxidative NHC catalysis. Synthetic utility of 2,2-disubstituted pyrrolinones is also demonstrated by facile conversion to pyrrolinone-fused γ-lactames in high yields.
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