Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 32, Pages 9414-9418Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201504964
Keywords
bicyclo[3; n; 1]alkanones; Conia-ene reaction; cycloheptanone; enolization; synergistic catalysis
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Funding
- National Basic Research Program of China (973 Program) [2011CB808600]
- National Natural Science Foundation of China [21172077, 21372086, 21422204]
- Guangdong Natural Science Foundation [2014A030313229, 10351064101000000]
- SRF for ROCS, State Education Ministry
- Fundamental Research Funds for the Central Universities, SCUT
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A highly efficient and practical synergistically metal/proton-catalyzed Conia-ene reaction for the synthesis of bicyclo[3.n.1]alkanones has been developed. This synergistic catalysis was successfully utilized in modifying natural compounds such as methyl dihydrojasmonate, ,-thujone, and 5-cholestan-3-one. Furthermore, the bridged carbonyl group of bicyclo[3.2.1]alkanones could be easily attacked by nucleophiles to give the ring-opened cycloheptenone products or bicyclo[4.2.1]amide in excellent yields. These reactions provide rapid access to a diverse range of cyclic structures from simple starting materials or naturally occurring compounds.
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