Studies towards dynamic kinetic resolution of 4-hydroxy-2-methylcyclopent-2-en-1-one and its E-O-trityloxime. Issue 32 (11th August 2016)

• Record Type: Journal Article
• Authors: Michalak, Karol; Wicha, Jerzy; Wójcik, Jacek
• Is Part Of: Tetrahedron. Volume 72:Issue 32(2016)
• Page Start: 4813
• Page End: 4820
• Publication Date: 2016-08-11
• Subjects: Dynamic kinetic resolution -- Ruthenium chloride cymene dimer -- Shvo's catalyst -- 3-Hydroxyl-cyclopent-2-en-1-one; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2016.06.047
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Dynamic kinetic resolution through metal complex induced racemization and Candida antarctica lipase mediated enantioselective acetylation of a model hydroxy-ketone: 4-hydroxy-2-methylcyclopent-2-en-1-one and its selected derivatives, has been studied. Racemization of the hydroxy-ketone was efficiently affected by [RuCl2 (cymene)]2 complex–triethylamine while Shvo's catalyst triggered an intramolecular redox process. Kinetic resolution of 4-hydroxy-2-methylcyclopent-2-en-1-one with C. antarctica under conditions compatible with [RuCl2 (cymene)]2 racemization failed to reach the efficiency threshold. However, dynamic kinetic resolution of its O -trityloxime using [RuCl2 (cymene)]2 –triethylamine and C. antarctica lipase–isopropenyl acetate combination, was successfully achieved. Graphical abstract: