Chemoselective and stereoselective lithium carbenoid mediated cyclopropanation of acyclic allylic alcohols
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Author/sDurán-Peña, María Jesús; Flores-Giubi, M. E.; Botubol Ares, José Manuel; M. Harwood, L.; González Collado, Isidro; Macías Sánchez, Antonio José; Hernández Galán, Rosario
SourceOrganic & Biomolecular Chemistry, 2016, 14, 2731
The reaction of geraniol with different lithium carbenoids generated from n-BuLi and the corresponding dihaloalkane has been evaluated. The reaction occurs in a chemo and stereoselective manner, which is consistent with a directing effect from the oxygen of the allylic moiety. Furthermore, a set of polyenes containing allylic hydroxyl or ether groups were chemoselectively and stereoselectively converted into the corresponding gem-dimethylcyclopropanes in one single step in moderate to good yields mediated by a lithium carbenoid generated in situ by the reaction of n-BuLi and 2,2-dibromopropane.