ENANTIOSELECTIVE CATALYSIS BY 1-(1-ISOQUINOLINVL)-2-NAPHTHALENEMETHANOL - AN ATROPISOMERICALLY CHIRAL N-O CHELATING LIGAND

Authors
BAKER RW REA SO SARGENT MV SCHENKELAARS EMC SKELTON BW WHITE AH
Citation
Rw. Baker et al., ENANTIOSELECTIVE CATALYSIS BY 1-(1-ISOQUINOLINVL)-2-NAPHTHALENEMETHANOL - AN ATROPISOMERICALLY CHIRAL N-O CHELATING LIGAND, Tetrahedron : asymmetry, 5(1), 1994, pp. 45-48
Citations number
12
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
5
Issue
1
Year of publication
1994
Pages
45 - 48
Database
ISI
SICI code
0957-4166(1994)5:1<45:ECB1>2.0.ZU;2-8
Abstract
Racemic 1-(1-isoquinolinyl)-2-naphthalenemethanol 6 has been prepared through a ligand coupling reaction of racemic 1-(tert-butylsulfinyl)is oquinoline 2 with the 1-naphthyl Grignard reagent 4. Resolution of the ligand 6 was achieved through chromatographic separation of the Noe-l actol(R) derivatives. The absolute configuration of (R)-(-)-6 was dete rmined by a single crystal X-ray study of the p-bromobenzoate derivati ve 9. (R)-(-)-6 enantioselectivity catalysed the addition of diethylzi nc to benzaldehyde, affording (S)-(-)-1-phenyl-1-propanol in 68% e.e.