1
Ethyl 2-hydroxy-2-phenylacetate: H NMR: d 1.22 (m, 3H),
Mallat and A. Baiker, J. Catal., 1998, 175, 569; A. Szabo, N. K u¨ nzle,
T. Mallat and A. Baiker, Tetrahedron: Asymmetry, 1999, 10, 61; J.
Keilitz, S. Nowag, J.-D. Marty and R. Haag, Adv. Synth. Catal., 2010,
3
5
.50 (bs, 1H, OH), 4.27 (m, 2H), 5.21 (bs, 1H), 7.29–7.52 (m,
+
H); mass: 180 (M ).
3
52, 1503–1511.
1
Ethyl 3-hydroxybutanoate: H NMR: d 1.22 (d, J = 7 Hz, 3H),
.28 (t, J = 7 Hz, 3H), 2.46 (dd, J = 2.5, 7.5 Hz, 2H), 4.15 (q, J =
Hz, 2H), 4.23 (m, 1H); mass: 133 (M ).
,1-Dimethoxypropan-2-ol: H NMR: d 1.15 (d, J = 5.5 Hz,
H), 2.30 (bs, 1H, OH), 3.43 (s, 3H), 3.47 (s, 3H), 3.75 (m, 1H),
.08 (d, J = 5.5 Hz, 1H); mass: 88 (M -32).
Dihydro-3-hydroxy-4,4-dimethylfuran-2(3H)-one: H NMR:
d 1.08 (s, 3H), 1.23 (s, 3H), 3.95–4.15 (m, 3H), 4.45 (bs, 1H,
10 N. Bonalumi, A. Vargas, D. Ferri and A. Baiker, Chem.–Eur. J., 2007,
13, 9236–9244; M. von Arx, N. Dummer, D. J. Willock, S. H. Taylor,
R. P. K. Wells, P. B. Wells and G. J. Hutchings, Chem. Commun.,
1
7
+
2
003, 1926–1927; G. Vayner, K. N. Houk and Y.-K. Sun, J. Am.
1
1
Chem. Soc., 2004, 126, 199–203; C. Exner, A. Pfaltz, M. Studer and
H.-U. Blaser, Adv. Synth. Catal., 2003, 345, 1253–1260; S.-K. Tian,
Y. Chen, J. Hang, L. Tang, P. Mcdoid and L. Deng, Acc. Chem. Res.,
2004, 37, 621–631.
3
4
+
1
1
1 M. Studer, H.-U. Blaser and C. Exner, Adv. Synth. Catal., 2003, 345,
4
5–65.
+
OH); mass: 131 (M ).
1
12 D. M. Rampulla and A. J. Gellman, Dekker Encylopedia of Nanosci.
1
Nanotech., 2004, 1113–1123.
-Phenylpropane-1,2-diol: H NMR: d 1.02 (m, 3H), 3.85,
.96 (2 m, 1H), 4.32, 4.67 (2d, 1H), 7.27–7.40 (m, 5H); mass:
1
3 A. Zecchina, E. Groppo and S. Bordiga, Chem.–Eur. J., 2007, 13,
440–2460.
14 C. Wang, Y. Hou, J. Kim and S. Sun, Angew. Chem., Int. Ed., 2007,
6, 6333–6335.
15 M. Wahl, M. von Arx, T. A. Jung and A. Baiker, J. Phys. Chem. B,
3
1
2
+
35 (M -18).
1
4
Ethyl 4,4,4-trifluoro-3-hydroxybutanoate: H NMR: d 1.3 (m,
H), 2.75 (m, 2H), 4.25 (m, 2H), 4.45 (m, 1H); mass: 187 (M ).
+
3
2
2
006, 110, 21777–21782; T. Burgi and A. Baiker, Acc. Chem. Res.,
004, 37, 909–917.
1
6 H.-U. Blaser and M. Studer, Acc. Chem. Res., 2007, 40, 1348–1356.
17 P. Maity, S. Basu, S Bhaduri and G. K. Lahiri, Adv. Synth. Catal.,
007, 349, 1955–1962.
8 M. Bartok, K. Felfoldi, B. Torok and T. Bartok, Chem. Commun.,
References
2
1
H. Brunner and W. Zettlemeyer, Handbook of Enantioselective
Catalysis with Transition Metal Compounds, Wiley-VCH, Weinheim,
993; R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley,
1
1
1
2
998, 2605–2606; D. Ferri, T. Burgi and A. Baiker, Chem. Commun.,
001, 1172–1173; D. Ferri, T. Burgi and A. Baiker, J. Chem. Soc.
1
New York, 1994.
Perkin Trans, 1999, 2, 1305–1311.
2
M. Heitbaum, F. Glorius and I. Escher, Angew. Chem., Int. Ed., 2006,
9 Z. Ma and F. Zaera, J. Am. Chem. Soc., 2006, 128, 16414–16415; Z.
Ma and F. Zaera, J. Phys. Chem. B, 2005, 109, 406–414; Z. Ma, I. Lee
and F. Zaera, J. Am. Chem. Soc., 2007, 129, 16083–16090; F. Hoxha,
L. Konigsmann, A. Vargas, D. Ferri, T. Mallat and A. Baiker, J.
Am. Chem. Soc., 2007, 129, 10582–10590; V. D. Carpentier, M.-A.
Laliberte, S. Lavoie, G. Mahieu and P. H. McBreen, J. Phys. Chem.
C, 2010, 114, 7291–7298; V. D. Carpentier, M.-A. Laliberte, Y. Pan,
G. Mahieu, S. Lavoie, G. Goubert, B. Hammer and P. H. McBreen,
J. Phys. Chem. C, 2011, 115, 1355–1360; S. Lavoie, M.-A. Laliberte
and P. H. McBreen, J. Am. Chem. Soc., 2003, 125, 15756–15757; S.
Lavoie, M.-A. Laliberte, I. Temprano and P. H. McBreen, J. Am.
Chem. Soc., 2006, 128, 7588–7593; S. Lavoie, M.-A. Laliberte, G.
Mahieu, V. D. Carpentier and P. H. McBreen, J. Am. Chem. Soc.,
4
5, 4732–4762; N. Erathodiyil, S. Ooi, A. M. Seayad, Y. Han, S. S.
Lee and J. Y. Ying, Chem.–Eur. J., 2008, 14, 3118–3125.
3
4
H.-J. Federsel, Nat. Rev. Drug Discovery, 2005, 4, 685–697.
H.-U. Blaser, Chem. Commun., 2003, 293–296; R. A. Sheldon, M.
Wallau, I. W. C. E. Arends and U. Schuchart, Acc. Chem. Res., 1998,
3
3
1, 485–493; P. McMorn and G. J. Hutchings, Chem. Soc. Rev., 2004,
3, 108–122.
J. M. Thomas and R. Raja, Acc. Chem. Res., 2008, 41, 708–720.
M. von Arx, T. Mallat and A. Baiker, Top. Catal., 2002, 19, 75–87;
G. Vayner, K. N. Houk and Y.-K. Sun, J. Am. Chem. Soc., 2004, 126,
99–203.
D. Astruc, F. Lu and J. R. Aranzaes, Angew. Chem., Int. Ed., 2005,
4, 7852–7872.
M. Studer, H.-U. Blaser and C. Exner, Adv. Synth. Catal., 2003, 345,
5–65.
H.-U. Blaser, H. P. Jalett, M. M u¨ ller and M. Studer, Catal. Today,
997, 37, 441; M. Studer, S. Burkhardt and H. U. Blaser, Chem.
Commun., 1999, 1727; B. T o¨ r o¨ k, K. Felf o¨ ldi, K. Balazsik and M.
Bartok, Chem. Commun., 1999, 1727; H.-U. Blaser and H. P. Jalett,
Stud. Surf. Sci. Catal., 1993, 78, 139; N. Sch u¨ rch, N. K u¨ nzle, T.
5
6
1
7
8
9
4
2
007, 129, 11668–11669; M.-A. Laliberte, S. Lavoie, B. Hammer, G.
Mahieu and P. H. McBreen, J. Am. Chem. Soc., 2008, 130, 5386–
387; S. Lavoie, G. Mahieu and P. H. McBreen, Angew. Chem., Int.
4
5
Ed., 2006, 45, 7404–7407; A. Vargas, D. Ferri, N. Bonalumi, T. Mallat
and A. Baiker, Angew. Chem., Int. Ed., 2007, 46, 3905–3908; W.-R.
Huck, T. Mallat and A. Baiker, Adv. Synth. Catal., 2003, 345, 255–
1
2
60; M. Bartok, M. Sutyinszki, K. Felfoldi and G. Szollosi, Chem.
Commun., 2002, 1130–1131.
3
074 | Green Chem., 2011, 13, 3070–3074
This journal is © The Royal Society of Chemistry 2011