Enantioselective catalysis by 1-(1-isoquinolinyl)-2-naphthalenemethanol: An atropisomerically chiral NO chelating ligand

• Published in: Tetrahedron: asymmetry Vol. 5; no. 1; pp. 45 - 48
• Main Authors: Baker, Robert W., Rea, Simon O., Sargent, Melvyn V., Schenkelaars, Elisabeth M.C., Skelton, Brian W., White, Allan H.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 1994; Elsevier; Elsevier Science
• Subjects: Aliphatic, non-condensed and condensed benzenic, and alicyclic compounds; Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; Chemistry, Physical; Condensed benzenic and aromatic compounds; Condensed matter: structure, mechanical and thermal properties; Exact sciences and technology; Organic chemistry; Organic compounds; Physical Sciences; Physics; Preparations and properties; Science & Technology; Structure of solids and liquids; crystallography; Structure of specific crystalline solids; ALDEHYDES; REAGENTS; LACTOLS; 2,3,3A,4,5,6,7,7A-OCTAHYDRO-7,8,8-TRIMETHYL-4,7-METHANOBENZOFURAN-2-YLPROTECTIV; Haloalcohol; Molecular structure; Nitrogen heterocycle; Benzaldehyde; Organic ligand; Experimental study; Asymmetric catalysis; Condensed benzenic compound; X ray diffraction; Primary alcohol; Chemical coupling; Grignard reagent; Optical resolution; Absolute configuration; Addition reaction; Bicyclic compound; Aromatic compound; Secondary alcohol; Organic compounds; Crystalline structure
• ISSN: 0957-4166; 1362-511X
• DOI: 10.1016/S0957-4166(00)80482-6

Racemic 1-(1-isoquinolinyl)-2-naphthalenemethanol 6 has been prepared through a ligand coupling reaction of racemic 1-( tert-butylsulfinyl)isoquinoline 2 with the 1-naphthyl Grignard reagent 4. Resolution of the ligand 6 was achieved through chromatographic separation of the Noe-lactol ® derivatives. The absolute configuration of ( R)-(-)- 6 was determined by a single crystal X-ray study of the p-bromobenzoate derivative 9. ( R)-(-)-6 enantioselecdvely catalysed the addition of diethylzinc to benzaldehyde, affording ( S)-(-)-1-phenyl-1-propanol in 68% e.e. Graphic