title: Highly enantioselective nickel-catalyzed intramolecular reductive cyclization of alkynones.
abstract: The first asymmetric nickel-catalyzed intramolecular reductive cyclization of alkynones is reported. A P-chiral monophosphine and triethylsilane were used as the ligand and the reducing reagent, respectively, to form a series of tertiary allylic alcohols bearing furan/pyran rings in excellent yields and enantioselectivities. This reaction has a broad substrate scope and enabled the efficient synthesis of dehydroxycubebin and chiral dibenzocyclooctadiene skeletons.
authors.affiliation: State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Rd, Shanghai 200032 (China).
authors.forename: Wenzhen
authors.initials: W
authors.lastname: Fu
authors.forename: Ming
authors.initials: M
authors.lastname: Nie
authors.forename: Aizhen
authors.initials: A
authors.lastname: Wang
authors.forename: Ziping
authors.initials: Z
authors.lastname: Cao
authors.forename: Wenjun
authors.initials: W
authors.lastname: Tang
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D007659:Ketones / Q000737:chemistry*; D008024:Ligands; D008968:Molecular Conformation; D009532:Nickel / Q000737:chemistry*; D010084:Oxidation-Reduction; D020005:Propanols / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D007659:Ketones; D008024:Ligands; D020005:Propanols; C006463:allyl alcohol; D009532:Nickel
keywords: P ligands; alkynones; asymmetric catalysis; cyclization; nickel