title: P-chiral o-phosphinophenol as a P/O hybrid ligand: preparation and use in Cu-catalyzed asymmetric conjugate addition of diethylzinc to acyclic enones.
abstract: [reaction: see text] (S)-2-(tert-Butylmethylphosphino)phenol and its methyl ether were synthesized from tert-butyldichlorophosphine via optically active phosphine-boranes as the intermediates. The former compound was used as a P/O hybrid ligand in the Cu-catalyzed asymmetric conjugate addition of diethylzinc to acyclic enones to achieve high enantioselectivity of up to 96%.
authors.affiliation: Department of Chemistry, Faculty of Science, Chiba University, Inage-ku, Japan.
authors.forename: Yukitoshi
authors.initials: Y
authors.lastname: Takahashi
authors.forename: Yoshikazu
authors.initials: Y
authors.lastname: Yamamoto
authors.forename: Kosuke
authors.initials: K
authors.lastname: Katagiri
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Danjo
authors.forename: Kentaro
authors.initials: K
authors.lastname: Yamaguchi
authors.forename: Tsuneo
authors.initials: T
authors.lastname: Imamoto
mesh_terms: D002384:Catalysis; D002599:Chalcone / Q000737:chemistry; D003300:Copper / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry*; D010758:Phosphorus / Q000737:chemistry*; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry*
chemical_list: D008024:Ligands; D010636:Phenols; D010720:Phosphines; C510998:o-phosphinophenol; D010758:Phosphorus; D002599:Chalcone; D003300:Copper; C044646:phosphine; D015032:Zinc; D010100:Oxygen