title: Development of asymmetric deacylative allylation.
abstract: Herein we present the development of asymmetric deacylative allylation of ketone enolates. The reaction directly couples readily available ketone pronucleophiles with allylic alcohols using facile retro-Claisen cleavage to form reactive intermediates in situ. The simplicity and robustness of the reaction conditions is demonstrated by the preparation of >6 g of an allylated tetralone from commercially available materials. Furthermore, use of nonracemic PHOX ligands allows intermolecular formation of quaternary stereocenters directly from allylic alcohols.
authors.affiliation: Department of Chemistry, The University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045-7582, United States.
authors.forename: Alexander J
authors.initials: AJ
authors.lastname: Grenning
authors.forename: Christie K
authors.initials: CK
authors.lastname: Van Allen
authors.forename: Tapan
authors.initials: T
authors.lastname: Maji
authors.forename: Simon B
authors.initials: SB
authors.lastname: Lang
authors.forename: Jon A
authors.initials: JA
authors.lastname: Tunge
mesh_terms: D002384:Catalysis; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D007659:Ketones; D009942:Organometallic Compounds; D010165:Palladium