P-Chiral o-Phosphinophenol as a P/O Hybrid Ligand:  Preparation and Use in Cu-Catalyzed Asymmetric Conjugate Addition of Diethylzinc to Acyclic Enones

• Published in: Journal of organic chemistry Vol. 70; no. 22; pp. 9009 - 9012
• Main Authors: Takahashi, Yukitoshi, Yamamoto, Yoshikazu, Katagiri, Kosuke, Danjo, Hiroshi, Yamaguchi, Kentaro, Imamoto, Tsuneo
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 28.10.2005; Amer Chemical Soc
• Subjects: Catalysis; Catalysts: preparations and properties; Chalcone - chemistry; Chemistry; Chemistry, Organic; Copper - chemistry; Exact sciences and technology; General and physical chemistry; Ligands; Molecular Structure; Oxygen - chemistry; Phenols - chemistry; Phosphines - chemistry; Phosphorus - chemistry; Physical Sciences; Science & Technology; Stereoisomerism; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; Zinc - chemistry; NICKEL-COMPLEXES; ALIPHATIC ENONES; PHOSPHORAMIDITES; PHOSPHINES; CHALCONES; DIALKYLZINC REAGENTS; ENANTIOSELECTIVE MICHAEL ADDITIONS; Catalytic reaction; Transition element complexes; Enantioselectivity; Tertiary phosphine; Ligand; Chiral compound; Transition metal Complexes; Copper complex; Phosphorus Organic compounds; Asymmetric synthesis; Phosphine borane; Addition reaction; Phenols; Chemical synthesis; Enone
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo051034y

(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%.