95548-93-9Relevant academic research and scientific papers
Attempted Kinetic Resolution of 1,2-Diols by Camphorquinone: Generation of (R)-(Chloromethyl)oxirane
Ellis, Martin K.,Golding, Bernard T.,Maude, Antony B.,Watson, William P.
, p. 747 - 755 (1991)
The epichlorohydrin (R)-(chloromethyl)oxirane has been prepared from rac-3-chloropropane-1,2-diol by means of the chiral ketone D-camphorquinone (1,7,7-trimethylbicycloheptane-2,3-dione).These reactions lead to intermediate dioxolanes which can be converted directly into oxiranes.This conversion was effected by reduction of the C-2-ketone of the dioxolane intermediate with sodium borohydride prior to reaction with hydrogen bromide-acetic acid followed by treatment of the resulting acetoxy bromide with sodium ethane-1,2-diolate.The diastereoselective formation of other dioxolanes was also investigated by reaction of D-camphorquinone with ethane-1,2-diol, propane-1,2-diol, and 3,3-dimethylbutane-1,2-diol.
Kinetic Resolution of 1,2-Diols with D-Camphorquinone; Preparation of (R)-(Chloromethyl)oxirane
Ellis, Martin K.,Golding, Bernard T.,Watson, William P.
, p. 1600 - 1602 (2007/10/02)
Acid-catalysed reaction of D-camphorquinone with racemic 1,2-diols (e.g. 3-chloropropane-1,2-diol) under kinetically controlled conditions yields a predominant diastereoisomeric acetal, that can be easily converted into an optically pure epoxide.
