The development of chiral catalysts is key to the production
of
enantiopure compounds, which are of great interest to the pharmaceutical
and fine chemical industries. The features of heterogeneous catalysts,
such as their high stability, easy separation, and facile reusability,
are particularly beneficial for practical applications. Supported
and chirally modified Pt catalysts have shown high potential in enantioselective
hydrogenation of α-keto esters. In this study, we report a highly
efficient and versatile Pt/B-SiO2 catalyst. Specially,
commercially available SiO2 support was modified with varying
amounts of boron via a facile impregnation method. For the enantioselective
hydrogenation of methyl pyruvate, 1 wt % Pt/B-SiO2 with
a molar ratio of B/Pt = 60 achieved 96% enantiomeric excess (ee) even
at H2 pressure of 0.1 MPa and maintained high enantioselectivity
during 10 consecutive cycles. For various α-keto esters, the
Pt/B-SiO2 catalyst also showed significantly higher activity
and enantioselectivity than unmodified Pt/SiO2. Moreover,
0.5 wt % Pt/B-SiO2 outperformed 5 wt % Pt/γ-Al2O3, one of the most efficient catalysts reported
for this reaction, despite its 10-times lower Pt loading. The enhanced
adsorption capability of B-SiO2 for a chiral modifier and
the resulting chiral modification of the Pt surface were found to
be responsible for the superior performance of Pt/B-SiO2. This strategy based on the facile surface modification of a commercially
available support material provides an opportunity to develop practical
and efficient heterogeneous enantioselective catalysts.