The scope of catalytic asymmetric hydroboration/oxidation with rhodium complexes of 1,1 '-(2-diarylphosphino-1-naphthyl)isoquinolines

Citation
H. Doucet et al., The scope of catalytic asymmetric hydroboration/oxidation with rhodium complexes of 1,1 '-(2-diarylphosphino-1-naphthyl)isoquinolines, CHEM-EUR J, 5(4), 1999, pp. 1320-1330
Citations number
81
Categorie Soggetti
Chemistry
Journal title
CHEMISTRY-A EUROPEAN JOURNAL
ISSN journal
09476539 → ACNP
Volume
5
Issue
4
Year of publication
1999
Pages
1320 - 1330
Database
ISI
SICI code
0947-6539(199904)5:4<1320:TSOCAH>2.0.ZU;2-Q
Abstract
Preformed cationic Rh complexes of the title ligands are effective for the asymmetric hydroboration/oxidation of vinylarenes at ambient temperature. T hese vinylarenes may carry E- or Z-beta substituents but not a substituents . Enantiomer excesses of up to 97% can be obtained in the most favourable c ases. The enantioselectivity is moderately sensitive to the structure of th e ligand: the difurylphosphino ligand gave superior results for electron-po or styrenes and the diphenylphosphino ligand the best results for electron- rich reactants. Mechanistic aspects are discussed.