title: Chemoselective and stereoselective lithium carbenoid mediated cyclopropanation of acyclic allylic alcohols.
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.
authors: Departamento de Química Orgánica, Facultad de Ciencias, Campus Universitario Puerto Real s/n, Torre sur, 4° planta. and Universidad de Cádiz, 11510, Puerto Real, Cádiz, Spain. rosario.hernandez@uca.es antoniojose.macias@uca.es.
authors: M J
authors: MJ
authors: Durán-Peña
authors: Departamento de Química Orgánica, Facultad de Ciencias, Campus Universitario Puerto Real s/n, Torre sur, 4° planta. and Universidad de Cádiz, 11510, Puerto Real, Cádiz, Spain. rosario.hernandez@uca.es antoniojose.macias@uca.es.
authors: M E
authors: ME
authors: Flores-Giubi
authors: Departamento de Química Orgánica, Facultad de Ciencias, Campus Universitario Puerto Real s/n, Torre sur, 4° planta. and Universidad de Cádiz, 11510, Puerto Real, Cádiz, Spain. rosario.hernandez@uca.es antoniojose.macias@uca.es.
authors: J M
authors: JM
authors: Botubol-Ares
authors: Department of Chemistry, University of Reading, Whiteknights, Reading RG6 6AD, UK.
authors: L M
authors: LM
authors: Harwood
authors: Departamento de Química Orgánica, Facultad de Ciencias, Campus Universitario Puerto Real s/n, Torre sur, 4° planta. and Universidad de Cádiz, 11510, Puerto Real, Cádiz, Spain. rosario.hernandez@uca.es antoniojose.macias@uca.es.
authors: I G
authors: IG
authors: Collado
authors: Departamento de Química Orgánica, Facultad de Ciencias, Campus Universitario Puerto Real s/n, Torre sur, 4° planta. and Universidad de Cádiz, 11510, Puerto Real, Cádiz, Spain. rosario.hernandez@uca.es antoniojose.macias@uca.es.
authors: A J
authors: AJ
authors: Macías-Sánchez
authors: Departamento de Química Orgánica, Facultad de Ciencias, Campus Universitario Puerto Real s/n, Torre sur, 4° planta. and Universidad de Cádiz, 11510, Puerto Real, Cádiz, Spain. rosario.hernandez@uca.es antoniojose.macias@uca.es.
authors: R
authors: R
authors: Hernández-Galán
mesh_terms: D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D008094:Lithium / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D003521:Cyclopropanes; D020005:Propanols; C030011:carbene; C006463:allyl alcohol; D008094:Lithium; D008697:Methane