Chemoselective and stereoselective lithium carbenoid mediated cyclopropanation of acyclic allylic alcohols

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Chemoselective and stereoselective lithium carbenoid mediated cyclopropanation of acyclic allylic alcohols

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Title: Chemoselective and stereoselective lithium carbenoid mediated cyclopropanation of acyclic allylic alcohols
Author: Durán-Peña, María Jesús; Flores-Giubi, M. E.; Botubol Ares, José Manuel; M. Harwood, L.; González Collado, Isidro; Macías Sánchez, Antonio José; Hernández Galán, Rosario
Departments: Química Orgánica
xmlui.dri2xhtml.METS-1.0.item-source: Organic & Biomolecular Chemistry, 2016, 14, 2731
Abstract: 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.
Handle: http://hdl.handle.net/10498/20593
Date: 2016

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Attribution-NonCommercial-NoDerivatives 4.0 Internacional Except where otherwise noted, this item's license is described as Attribution-NonCommercial-NoDerivatives 4.0 Internacional