Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 25, Issue 20, Pages 5154-5157Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201806416
Keywords
8-aminoquinoline; C(sp(3))-H functionalization; cyclobutanes; palladium; verbenone
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Funding
- Wenner-Gren foundations
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This work demonstrates how a series of complex, chiral cyclobutane derivatives can be accessed in four steps from the terpene verbenone through the application of a directed C-H functionalization approach. The developed synthetic route involved an 8-aminoquinoline-directed C(sp(3))-H arylation as the key step, and this reaction could be carried out with a wide range of aryl and heteroaryl iodides to furnish a variety of cyclobutane products with three contiguous stereocenters. Moreover, it was shown that the 8-aminoquinoline auxiliary could be effectively removed from the cyclobutane derivatives using an ozonolysis-based cleavage method.
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