Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 9, Pages 2425-2430Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201304839
Keywords
catalysis; cyclopropanes; Diels-Alder reaction; gold; tandem reactions
Categories
Funding
- NNSFC [21172077, 21372086]
- Program for New Century Excellent Talents in University [NCET-10-0403]
- National Basic Research Program of China (973) [2011CB808600]
- Changjiang Scholars and Innovation Team Project of the Ministry of Education
- SRF for ROCS, State Education Ministry
- Guangdong NSF [10351064101000000]
- Fundamental Research Funds for the Central Universities
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A bioinsipred gold-catalyzed tandem Diels-Alder/Diels-Alder reaction of an enynal and a 1,3-diene, forming the highly-strained benzotricyclo[3.2.1.0(2,7)]octane skeleton, was reported. In contrast, a Diels-Alder/Friedel-Crafts tandem reaction occurred instead when silver salts were used as the catalyst. Although both reactions experienced the similar Diels-Alder reaction of a pyrylium intermediate with a 1,3-diene, they have different reaction mechanisms. The former proceeded with a stepwise Diels-Alder reaction, while the latter one with a concerted one.
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