Chemoselective and stereoselective lithium carbenoid\ud mediated cyclopropanation of acyclic allylic alcohols

Autor: Durán-Peña, M. J., Flores-Giubi, M. E., Botubol-Ares, J. M., Harwood, Laurence M., Collado, I. G., Macías-Sánchez, A. J., Hernández-Galán, R.
Jazyk: angličtina
Rok vydání: 2016
ISSN: 1477-0520
Popis: 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 gemdimethylcyclopropanes in one single step in moderate to good yields mediated by a lithium carbenoid generated in situ by reaction of n-BuLi and 2,2-dibromopropane.
Databáze: OpenAIRE