G. Cavicchio, P. Bravo*, V. Marchetti
Sep 1, 1991
Citations
0
Influential Citations
0
Citations
Journal
Journal of Fluorine Chemistry
Abstract
Abstract As part of a program directed towards developing an asymmetric approach to fluorosubstituted organic molecules 1 , we have observed an efficient transfer of chirality from sulphur to the central carbon atom when chiton 1 is reacted with diazomethane. 2-(Fluoromethyl)-2-[(4- methylphenylsulphinyl)methyl]oxirane 2 was obtained in good yield and with high d.e.: 2-(Fluoromethyl)oxirane 2 , whose crystal and molecular structure will be provided, as well as 2-(chloromcthyl)- and 2-(bromomethyl)- analogs, prepared in the same way, can be considered as a potential carbinols bearing three differently functionalized methylens, each one with a distinct reactivity. Some synthetically useful elaborations of 2 , i.e. transformation of the sulphinyl chiral auxiliary into other functional groups and regioselective opening of the oxirane ring to give derivatives as 3 , will be presented. A possible explanation of the observed diastereoselection, as well as the influence on the reaction outcome of electron-withdrawing groups in α to the carbonyl of the starting ketone will be discussed.