Communication
ChemComm
Table 3 Asymmetric hydrogenation of various a-ketoesters catalyzed by
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a
Unless otherwise noted, the reactions were performed under the optimized
conditions; the conversion rate was determined by GC with cyclohexane as
the internal standard; the unit of TOF is defined as per hour; the ee% were
determined by chiral GC; all reactions were repeated three times. b 1.20 mg
(3.56 Â 10À3 mmol) of Pt nanoparticles, substrate/CILPEG-CD/Pt = 100 : 7.5 : 1,
toluene (1.0 g), n-heptane (0.3 g), and glacial acetic acid (1.6 g). c 0.60 mg
(1.78 Â 10À3 mmol) of Pt nanoparticles, substrate/CILPEG-CD/Pt = 200 : 15 : 1,
toluene (1.0 g), n-heptane (0.3 g), and glacial acetic acid (1.6 g). d 1.20 mg
(3.56 Â 10À3 mmol) of Pt nanoparticles, substrate/CILPEG-CD/Pt = 50 : 7.5 : 1,
toluene (1.0 g), n-heptane (0.3 g), and glacial acetic acid (1.6 g). e 0.6 mg
(1.78 Â 10À3 mmol) of Pt nanoparticles, substrate/CILPEG-CD/Pt = 1000 : 15 : 1,
toluene (1.0 g), n-heptane (0.3 g), and glacial acetic acid (1.3 g).
´
(c) M. Bartok, Chem. Rev., 2010, 110, 1663.
¨
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16 (S)-Ethyl Lactate was purchased from J&K Scientific.
17 (a) E. Plessers, D. E. De Vos and M. B. J. Roeffaers, J. Catal., 2016,
340, 136; (b) W. Li, Y. Wang, P. Chen, M. Zeng, J. Jiang and Z. Jin,
Catal. Sci. Technol., 2016, 6, 7386; (c) J. Wen, J. Jiang and X. Zhang,
Org. Lett., 2016, 18, 4451.
18 (S)-Methyl lactate (S-2) was purchased from Accela; (R)-2-hydroxy-4-
phenylbutyric acid ethyl ester (12), methyl (R)-(À)-mandelate (15),
and ethyl (R)-(À)-mandelate (16) were purchased from Adamas; (S)-
3-hydroxy-4,4-dimethyldihydrofuran-2(3H)-one (S-20) was purchased
from Alfa Aesar.
Notes and references
1 For selected reviews, see: (a) A. Roucoux, J. Schulz and H. Patin,
Chem. Rev., 2002, 102, 3757; (b) S. Hu¨bner, J. G. de. Vries and
V. Farina, Adv. Synth. Catal., 2016, 358, 3.
´
2 For selected examples, see: (a) I. Favier, M. Gomez, G. Muller,
D. Picurelli, A. Nowicki, A. Roucoux and J. Bou, J. Appl. Polym. Sci.,
Chem. Commun.
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