title: Total synthesis of (R,R,R)-α-tocopherol through asymmetric Cu-catalyzed 1,4-addition.
abstract: By introducing a disposable activating substituent at C-3, the asymmetric 1,4-addition to a notoriously unreactive 2-substituted chromenone was achieved with high levels of (2R)-stereoselectivity in the presence of a chiral Cu(I)-phosphoramidite complex as a catalyst. This paved the way for an efficient and conceptually novel synthesis of (R,R,R)-α-tocopherol from readily available starting materials.
authors.affiliation: Universität zu Köln, Department für Chemie, Greinstrasse 4, 50939 Köln (Germany).
authors.forename: Andreas Ole
authors.initials: AO
authors.lastname: Termath
authors.forename: Hanna
authors.initials: H
authors.lastname: Sebode
authors.forename: Waldemar
authors.initials: W
authors.lastname: Schlundt
authors.forename: René T
authors.initials: RT
authors.lastname: Stemmler
authors.forename: Thomas
authors.initials: T
authors.lastname: Netscher
authors.forename: Werner
authors.initials: W
authors.lastname: Bonrath
authors.forename: Hans-Günther
authors.initials: HG
authors.lastname: Schmalz
mesh_terms: D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D024502:alpha-Tocopherol / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D003300:Copper; D024502:alpha-Tocopherol
keywords: asymmetric conjugate addition; chiral ligands; chromenones; copper catalysis; vitamin E