Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 73, Issue 19, Pages 7721-7730Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo8014769
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Funding
- MEC [CTQ2007-60745/BQU, CSD2006-0003]
- AGAUR [SGR 00993]
- ICIQ Foundation
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Gold (1)-catalyzed addition of carbon nucleophiles to 1,6-enynes gives two different type of products by reaction at the cyclopropane or at the carbene carbons of the intermediate cyclopropyl gold carbenes. The 5-exo-dig cyclization is followed by most 1,6-enynes, although those bearing internal alkynes and alkenes react by the 6-endo-dig pathway. The cyclopropane versus carbene site-selectivity can be controlled in some cases by the ligand on the gold catalyst. In addition to electron-rich arenes and heteroarenes, allylsilanes and 1,3-dicarbonyl compounds can be used as the nucleophiles, In the reaction of 1,5-enynes with carbon nucleophiles, the 5-endo-dig pathway is preferred.
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