title: Enantioselective Palladium-Catalyzed Carbonylative Carbocyclization of Enallenes via Cross-Dehydrogenative Coupling with Terminal Alkynes: Efficient Construction of α-Chirality of Ketones.
abstract: An enantioselective PdII/Brønsted acid-catalyzed carbonylative carbocyclization of enallenes ending with a cross-dehydrogenative coupling (CDC) with a terminal alkyne was developed. VAPOL phosphoric acid was found as the best co-catalyst among the examined 28 chiral acids, for inducing the enantioselectivity of α-chiral ketones. As a result, a number of chiral cyclopentenones were easily synthesized in good to excellent enantiomeric ratio with good yields.
authors.affiliation: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-106 91, Stockholm, Sweden.
authors.forename: Bin
authors.initials: B
authors.lastname: Yang
authors.affiliation: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-106 91, Stockholm, Sweden.
authors.forename: Youai
authors.initials: Y
authors.lastname: Qiu
authors.affiliation: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-106 91, Stockholm, Sweden.
authors.forename: Tuo
authors.initials: T
authors.lastname: Jiang
authors.affiliation: Department of Chemistry, Michigan State University, MI, 48824, East Lansing, USA.
authors.forename: William D
authors.initials: WD
authors.lastname: Wulff
authors.affiliation: Department of Chemistry, Michigan State University, MI, 48824, East Lansing, USA.
authors.forename: Xiaopeng
authors.initials: X
authors.lastname: Yin
authors.affiliation: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-106 91, Stockholm, Sweden.
authors.forename: Can
authors.initials: C
authors.lastname: Zhu
authors.affiliation: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-106 91, Stockholm, Sweden.
authors.forename: Jan-E
authors.identifier: 0000-0001-8462-4176
authors.initials: JE
authors.lastname: Bäckvall
keywords: asymmetric carbocyclization; enallenes; homogeneous catalysis; oxidation; palladium