期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 54, 期 46, 页码 13739-13742出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201506907
关键词
amides; multicomponent reactions; radicals; titanium; umpolung
资金
- NSF of China [21172183, 21472157]
- Fundamental Research Funds for Central Universities [2013121016]
- SRF for ROCS, SEM
- NFFTBS [J1310024]
- Program for Changjiang Scholars and Innovative Research Team in University (PCSIRT)
An umpolung Mannich-type reaction of secondary amides, aliphatic aldehydes, and electrophilic alkenes has been disclosed. This reaction features the one-pot formation of CN and CC bonds by a titanocene-catalyzed radical coupling of the condensation products, from secondary amides and aldehydes, with electrophilic alkenes. N-substituted -amido-acid derivatives and -amido ketones can be efficiently prepared by the current method. Extension to the reaction between ketoamides and electrophilic alkenes allows rapid assembly of piperidine skeletons with -amino quaternary carbon centers. Its synthetic utility has been demonstrated by a facile construction of the tricyclic core of marine alkaloids such as cylindricineC and polycitorol A.
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