124601-22-5Relevant academic research and scientific papers
On the Synthesis of Optically Pure Monofluoro cyclohexanol Derivatives by the Fluorinated Sulfoxide Chiron Route
Arnone, Alberto,Bravo, Pierfrancesco,Frigerio, Massimo,Viani, Fiorenza,Cavicchio, Giancarlo,Crucianelli, Marcello
, p. 12361 - 12374 (2007/10/02)
Monofluorocyclohexanols 1 are obtained in optically pure form through radical cyclization of gem-chlorofluoroheptenols 2 which derive from the condensation of α-lithium derivative of sulfoxide of 3 on racemic ethyl chlorofluoroacetate 4, and hydride-promo
Homochiral Fluoro-organic Compounds. Part 12. α-Hydroxy β-Fluoro Aldehydes and Esters, Fluoro Epoxides and Glycols from Fluorinated Sulphinyl Chirons
Bravo, Pierfrancesco,Piovosi, Elena,Resnati, Giuseppe
, p. 1201 - 1208 (2007/10/02)
α-Fluoro α'-sulphinyl ketones carrying an α'-alkyl or α'-aryl substituent have been reduced with high 1,2- or 1,3-induced diastereoselectivity to give the corresponding α-fluoro α'-sulphinyl secondary alkohols.The chiral sulphinyl auxiliary agent was removed by first selective reduction to a thio group, then by methylation to a sulphonium ion and finally through SN2 removal by the adjacent secondary alcohol.It is therefore possible to obtain, in an optically pure form, α-fluoro epoxides which are chiral at both the carbon atoms of the oxirane ring, or at the α-fluorinated carbon and at adjacent oxirane carbon.Furthermore, homochiral α-fluorinated vicinal glycols, β-fluoro α-hydroxy aldehydes, and β-fluoro α-hydroxy esters, which may contain the fluorohydrin moiety with syn or anti relative stereochemistry, have been obtained in an optically pure form from the corresponding α-fluoro α'-sulphinyl secondary alcohols by use of the varied reactivity of the sulphinyl group.
