Chiral-anion-dependent inversion of diastereo- and enantioselectivity in carbonyl crotylation via ruthenium-catalyzed butadiene hydrohydroxyalkylation.
J Am Chem Soc
; 134(51): 20628-31, 2012 Dec 26.
Article
em En
| MEDLINE
| ID: mdl-23234459
ABSTRACT
The ruthenium catalyst generated in situ from H(2)Ru(CO)(PPh(3))(3), (S)-SEGPHOS, and a TADDOL-derived phosphoric acid promotes butadiene hydrohydroxyalkylation to form enantiomerically enriched products. Notably, the observed diastereo- and enantioselectivity is the opposite of that observed using BINOL-derived phosphate counterions in combination with (S)-SEGPHOS, the same enantiomer of the chiral ligand. Match/mismatch effects between the chiral ligand and the chiral TADDOL-phosphate counterion are described. For the first time, single-crystal X-ray diffraction data for a ruthenium complex modified by a chiral phosphate counterion are reported.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Rutênio
/
Butadienos
Idioma:
En
Ano de publicação:
2012
Tipo de documento:
Article