52188-73-5Relevant articles and documents
Chemoselective and stereoselective lithium carbenoid mediated cyclopropanation of acyclic allylic alcohols
Durán-Pe?a,Flores-Giubi,Botubol-Ares,Harwood,Collado,Macías-Sánchez,Hernández-Galán
, p. 2731 - 2741 (2016)
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.
Titanium carbenoid-mediated cyclopropanation of allylic alcohols: Selectivity and mechanism
Durán-Pe?a,Botubol-Ares,Hanson,Hernández-Galán,Collado
, p. 6325 - 6332 (2015/06/08)
A new method for the chemo- and stereoselective conversion of allylic alcohols into the corresponding cyclopropane derivatives has been developed. The cyclopropanation reaction was carried out with an unprecedented titanium carbenoid generated in situ from Nugent's reagent, manganese and methylene diiodide. The reaction involving the participation of an allylic hydroxyl group, proceeded with conservation of the alkene geometry and in a high diastereomeric excess. The scope, limitations and mechanism of this metal-catalysed reaction are discussed. This journal is
Oxidative cyclization of diols derived from 1,5-dienes: Formation of enantiopure cis-tetrahydrofurans by using catalytic osmium tetroxide; formal synthesis of (+)-cis-solamin
Donohoe, Timothy J.,Butterworth, Sam
, p. 4766 - 4768 (2007/10/03)
(Chemical Equation Presented) High yields and high levels of stereocontrol are observed in the oxidative cyclization of vicinal diols using catalytic amounts of a transition metal (see scheme; TFA = trifluoroacetic acid). The product stereochemistry is co