72569-64-3Relevant academic research and scientific papers
Preparation and regioselective SN2′ reaction of novel gem-difluorinated vinyloxiranes with RLi
Ueki, Hisanori,Chiba, Takashi,Yamazaki, Takashi,Kitazume, Tomoya
, p. 7616 - 7627 (2007/10/03)
A series of hitherto unknown 3,4-epoxy-1,1-difluorobutenes were prepared from the readily accessible α,β-epoxy ketones and these compounds were found to undergo regioselective SN2′ reactions with hard RLi nucleophiles occurring at the highly positively charged terminal fluorine-possessing sp2 carbon atom in quite sharp contrast to the cases of the corresponding nonfluorinated vinyloxiranes which only attained a low level of regioselectivity. Addition of HMPA substantially improved the products' olefinic stereoselectivity. Theoretical calculations were used to qualitatively explore the nature of selectivity in these reactions.
Hydrozirconation of alkenyloxirane derivatives: Preparation of cycloalkylmethanols
Harada, Susumu,Kowase, Noboru,Tabuchi, Nobuhito,Taguchi, Takeo,Dobashi, Yasuo,Dobashi, Akira,Hanzawa, Yuji
, p. 753 - 766 (2007/10/03)
Cyclopentyl and cyclopropylmethanol derivatives were efficiently prepared through a chemoselective hydrozirconation reaction of (1- butenyl)oxirane and vinyloxirane with Cp2ZrHCl. However, the attemped reaction of (1-pentenyl)oxirane or (1-propenyl)oxirane failed to yield cyclohexyl or cyclobutylmethanols. The ring formation was stereospecific and proceeded with the inversion of the configuration at the reacting oxirane carbon. The origin of stereospecificity and the stereoselectivity in the formation of cyclopropylmethanols was presumed by the approach of the Schwartz reagent from the less hindered site of the stable gauche-conformer of the vinyloxirane compound in the transition state. (Cyclopropylmethyl)amine derivatives were also prepared by the treatment of vinylaziridine derivatives with Cp2ZrHCl.
FACILE PREPARATION OF γ-CHLORO-SUBSTITUTED ALLYLMETALLIC REAGENTS AND THEIR REACTIONS. STEREOSELECTIVE ACCESS TO CIS-VINYLOXIRANES
Hosomi, Akira,Kohra, Shinya,Tominaga, Yoshinori,Ando, Masamoto,Sakurai, Hideki
, p. 3058 - 3061 (2007/10/02)
The title compounds are readily prepared from metallated allyl chloride and organotin chloride or organoaluminum chloride.After treatment with a base, they react with aldehydes in highly regio- and diastereo-selective modes, giving cis-vinyloxiranes selectively.Keywords -- lithiated allyl chloride; Z-γ-chloroallyltrimethyltin; γ-chloroallyldiethylaluminum; stereoselective synthesis; syn-chlorohydrin; cis-vinyloxirane
THE HIGHLY STEREOSELECTIVE SYNTHESIS OF CIS-VINYLOXIRANES
Yamaguchi, Masahiko,Mukaiyama, Teruaki
, p. 237 - 240 (2007/10/02)
In the presence of triethylaluminum, oxyallyl anions derived from 2-allyloxybenzimidazoles react with aldehydes in highly regio- and stereoselective manner to afford α-adducts in good yields.The adducts are stereospecifically converted to cis-vinyloxiranes in good yields.
