Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 21, Pages 7079-7083Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201601195
Keywords
catalysis; cycloaddition; enynes; rhodium; seven-membered rings
Categories
Funding
- University of Wisconsin-Madison
- NSF [CHE-1464754, CHE-1059084]
- Tianjin Natural Science Foundation [14JCYBJC20100]
- MOE Innovation Teams of China [IRT-13R30, IRT13022]
- University of Pittsburgh
- Chinese Scholarship Council
- National Natural Science Foundation of China [21302168]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1361104, 1464754] Funding Source: National Science Foundation
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By switching the position of the alkene and alkyne, a new type of 3-acyloxy-1,4-enyne (ACE) five-carbon building block was developed for Rh-catalyzed intramolecular [5+2] cycloaddition. An electron-withdrawing acyl group on the alkyne termini of the ACE was essential for a regioselective 1,2-acyloxy migration. This new method provided bicyclic [5.3.0]decatrienes that are different from previous methods because of the positions of the alkenes and the acyloxy group. Multiple mechanistic pathways become possible for this new [5+2] cycloaddition and they are investigated by computational studies.
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