title: Enantioselective synthesis of 4-heterosubstituted cyclopentenones.
abstract: Racemic 4-hydroxycyclopentenone, readily derived from furfuryl alcohol, can be transformed via its O-Boc derivative to 4-acyloxy, 4-aryloxy-, 4-amino-, or 4-thio-substituted cyclopentenones with high enantioselectivity by palladium-catalyzed kinetic resolution via nucleophilic allylic substitutions. Applying this methodology, a short formal synthesis of ent-noraristeromycin was readily accomplished.
authors.affiliation: Institut für Organische Chemie, Universitaet Regensburg, Universitätsstrasse 31, 93053 Regensburg, Germany.
authors.forename: Kathrin
authors.initials: K
authors.lastname: Ulbrich
authors.forename: Peter
authors.initials: P
authors.lastname: Kreitmeier
authors.forename: Tirayut
authors.initials: T
authors.lastname: Vilaivan
authors.forename: Oliver
authors.initials: O
authors.lastname: Reiser
mesh_terms: D002384:Catalysis; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C548046:4-hydroxycyclopentenone; D003517:Cyclopentanes; D005663:Furans; D010165:Palladium; C013905:cyclopentenone; C018675:tetrahydrofurfuryl alcohol