The successive double allylation of cyclopropenes with allylindium sesquiiodide and allyl iodide proceeded with a cis-addition mode in the presence of other organometallics (e.g. Grignard reagent, cuprate, Et(2)Zn and Et(3)Al), giving the corresponding cis-diallylcyclopropanes in high yields.
Cyclopropane derivatives Q 0021Cis Double Allylation of Cyclopropenes Using Cyclopropylindium Reagents. -The double allylation of cyclopropenes (I) proceeds in a stepwise manner. Allylation with allylindium sesquiiodide, genearated in situ, is followed by metalation and a second allylation with allyl iodide. The reaction proceeds with excellent cis-selectivity for the diallyl unit, while the configuration relative to the third stereocenter is strongly influenced by the C-3 substituent structure. No reaction takes place in the presence of strongly chelating hydroxyalkyl substituents. -(HIRASHITA*, T.; SHIRAKI, F.; ONISHI, K.; OGURA, M.; ARAKI, S.; Org.
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