Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 18, Issue 23, Pages 7296-7305Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201103809
Keywords
alkenes; allenes; enynes; halogens; halolactonization; organocatalysts
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Funding
- University of Wisconsin
- Petroleum Research Fund [48092-G1]
- Amgen
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New organocatalysts have been developed for the enantioselective halolactonization of (Z)-1,3-enynes and 1,1-disubstituted alkenes. In the case of 1,3-enynes, the carboxylate nucleophile and halogen electrophile were added to the conjugated p-system from the same face. Up to 99?% ee was achieved for the 1,4-syn-bromolactonization of conjugated (Z)-1,3-enynes. Based on the results from the enyne halolactonization, a second generation of catalysts was designed for simple olefins. Up to 91?% ee was observed for chlorolactonization of 1,1-disubstituted alkenes. The catalysts developed for the enantioselective halolactonization of both enynes and alkenes are composed of a cinchona alkaloid skeleton tethered to a urea group.
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