2 research outputs found
Chiral Surfactant-Type Catalyst for Asymmetric Reduction of Aliphatic Ketones in Water
A novel chiral surfactant-type catalyst is developed.
Micelles
formed in water by association of the catalysts themselves, and this
was confirmed by TEM analyses. Asymmetric transfer hydrogenation of
aliphatic ketones catalyzed by the chiral metallomicellar catalyst
gave good to excellent conversions and remarkable stereoselectivities
(up to 95% ee). Synergistic effects between the metal-catalyzed center
and the hydrophobic microenvironment of the core in the metallomicelle
led to high enantioselectivities
Chiral Surfactant-Type Catalyst: Enantioselective Reduction of Long-Chain Aliphatic Ketoesters in Water
A series of amphiphilic ligands were
designed and synthesized.
The rhodium complexes with the ligands were applied to the asymmetric
transfer hydrogenation of broad range of long-chained aliphatic ketoesters
in neat water. Quantitative conversion and excellent enantioselectivity
(up to 99% ee) was observed for α-, β-, γ-, δ-
and ε-ketoesters as well as for α- and β-acyloxyketone
using chiral surfactant-type catalyst <b>2</b>. The CH/Ï€
interaction and the strong hydrophobic interaction of long aliphatic
chains between the catalyst and the substrate in the metallomicelle
core played a key role in the catalytic transition state. Synergistic
effects between the metal-catalyzed site and the hydrophobic microenvironment
of the core in the micelle contributed to high stereoselectivity