Kinetic racemate resolution of saturated three-membered heterocycles

W. Keim (Inventor), M. Brunner (Inventor), L. Mussmann (Inventor), D. Vogt (Inventor)

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    A process for the kinetic racemate resolution of saturated three-membered heterocycles is characterised in that a) a monosubstituted saturated three-membered heterocycle, b) in the presence of a Lewis acid complex of a metal from Group IVa with a chiral alcohol or amino alcohol, c) is reacted with a nucleophile or a combination of a nucleophile and a compound which reacts further with the primary ring-opening product of the saturated three-membered heterocycle to give a product which is stable under reaction conditions. The process according to the invention allows wide access to various enantiomerically pure or enantiomerically enriched ring-opening products of saturated three-membered heterocycles, in particular oxiranes. In principle, both enantiomers are available for further reaction. A particular advantage in the synthesis of carbonates from oxiranes using CO2/iodide is that both reaction products can be reacted with the same reagents to give the same products.
    Original languageEnglish
    Patent numberDE4333686
    Publication statusPublished - 6 Apr 1995


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