title: Enantiopure dihalocyclopropyl alcohols and esters by lipase catalyzed kinetic resolution.
abstract: Four halogenated cyclopropane derivatives with a side chain containing a primary (1 and 2) or secondary (3 and 4) alcohol moiety were subject to kinetic resolution catalyzed by lipases. Two of them containing secondary alcohol groups gave excellent results with Candida antarctica lipase B with E-values around 1000. Two enantiopure alcohols and two enantiopure butanoates are described: (1S,1'S)-1-(2',2'-dichloro-3',3'-dimethylcyclopropyl) ethanol (3), the corresponding (1R,1'R)-butanoate (3b) and (1S,1'S)-1-(1'-methyl-2',2'-dibromocyclopropyl) ethanol (4) and the corresponding (1R,1'R)-butanoate (4b).
authors.affiliation: Department of Chemistry, Norwegian University of Science and Technology, 7491 Trondheim, Norway. Electronic address: elisabeth.e.jacobsen@ntnu.no.
authors.forename: Elisabeth Egholm
authors.initials: EE
authors.lastname: Jacobsen
authors.forename: Mohammed Farrag
authors.initials: MF
authors.lastname: el-Behairy
authors.forename: Lars
authors.initials: L
authors.lastname: Skattebøl
authors.forename: Thorleif
authors.initials: T
authors.lastname: Anthonsen
mesh_terms: D000438:Alcohols / Q000737:chemistry / Q000378:metabolism*; D055162:Biocatalysis; D002087:Butyrates / Q000737:chemistry / Q000378:metabolism*; D018360:Crystallography, X-Ray; D003521:Cyclopropanes / Q000737:chemistry* / Q000378:metabolism*; D004800:Enzymes, Immobilized / Q000378:metabolism*; D004951:Esterification; D005656:Fungal Proteins / Q000378:metabolism*; D007700:Kinetics; D008049:Lipase / Q000378:metabolism*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D002087:Butyrates; D003521:Cyclopropanes; D004800:Enzymes, Immobilized; D005656:Fungal Proteins; D008049:Lipase; C431349:lipase B, Candida antarctica
keywords: Enantiopure dihalocyclopropyl derivatives; Kinetic resolution; Lipase catalysis