Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 49, Pages 13592-13595Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201407532
Keywords
delta-amino-beta-ketoesters; disulfonimides; organocatalysis; vinylogous Mukaiyama-Mannich reaction
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Funding
- Max-Planck-Society
- European Research Council
- Fonds der Chemischen Industrie
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An organocatalytic asymmetric synthesis of delta-amino-beta-ketoester derivatives has been developed. A chiral disulfonimide (DSI) serves as a highly efficient precatalyst for a vinylogous Mukaiyama-Mannich reaction of readily available dioxinone-derived silyloxydienes with N-Boc-protected imines, delivering products in excellent yields and enantioselectivities. The synthetic utility of this reaction is illustrated in various transformations, including a new C-C bond-forming reaction, which provide useful enantioenriched building blocks. The methodology is applied in a formal synthesis of (-)-lasubin.
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