Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 6, Pages 2780-2785Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo302751p
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- Deutsche Forschungsgemeinschaft (DFG)
- Fonds der Chemischen Industrie (FCI)
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The electrophilic cyclization of 3-silyloxy-1,5-enynes and 3-silyloxy-1,6-enynes was investigated. In the presence of N-iodosuccinimide (NIS), the title compounds are transformed under metal-free conditions into five-membered carbocycles with all-carbon stereogenic centers following a sequence of iodonium activation of the triple bond, carbocyclization, and pinacol-type 1,2-shift.
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