288
J.-J. Wu et al. / Tetrahedron 67 (2011) 285e288
(
(
m, 5H). 13C NMR:
relative intensity, %) 153 (M , 21), 124 (100), 109 (7).
d
30.0, 62.5, 126.4, 129.0, 129.9, 135.4. MS (EI) m/z
3. (a) Velders, G. J. M.; Fahey, D. W.; Daniel, J. S.; McFarland, M.; Andersen, S. O.
PNAS 2009, 106, 10949e10954; (b) Molina, M. J.; Rowland, F. S. Nature 1974, 249,
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810e812; (c) Shine, K. P.; Sturges, W. T. Science 2007, 315, 1804e1805.
4
. (a) Amii, H.; Uneyama, K. Chem. Rev. 2009, 109, 2119e2183 and references cited
therein; (b) Matsubara, K.; Ishibashi, T.; Koga, Y. Org. Lett. 2009, 11, 1765e1768;
4
.3.3. N-Benzylethylamine (19).22 Light-yellow liquid. 1H NMR:
1.17 (t, J¼7.1 Hz, 3H), 1.90 (s, 1H), 2.72 (t, J¼7.2 Hz, 2H), 3.83 (s, 2H),
(
c) Perutz, R. N. Science 2008, 321, 1168e1169; (d) Driver, T. G. Angew. Chem., Int.
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009, 74, 2850e2853.
d
7
.25e7.36 (m, 5H). 13C NMR:
d
15.2, 43.6, 53.9, 126.9, 128.2, 128.4,
2
þ
140.2. MS (EI) m/z (relative intensity, %) 135 (M , 16), 120 (37), 91
5. (a) Mazurek, U.; Schwarz, H. Chem. Commun. 2003, 1321e1326; (b) Torrens, H.
Coord. Chem. Rev. 2005, 249, 1957e1985; (c) Schaub, T.; Backes, M.; Radius, U. J.
Am. Chem. Soc. 2006, 128, 15964e15965; (d) Meier, G.; Braun, T. Angew. Chem.,
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(
100).
4
d
.3.4. 3-Phenylbutan-1-ol (20).23 Light-yellow liquid. 1H NMR:
1.31 (d, J¼7.0 Hz, 3H),1.50 (s,1H),1.88 (m, J¼7.0 Hz, 2H), 2.87e2.96
13
(
m, 1H), 3.53e3.63 (m, 2H), 7.21e7.35 (m, 5H). C NMR: d 22.4,
3
6.5, 41.0, 61.2, 126.1, 127.0, 128.5, 146.9. MS (EI) m/z (relative in-
þ
6
. (a) Douvris, C.; Nagaraja, M.; Chen, C.; Foxman, B. M.; Ozerov, O. V. J. Am. Chem.
Soc. 2010, 132, 4946e4953; (b) Reade, S. P.; Mahon, M. F.; Whittlesey, M. K. J.
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P. L. J. Am. Chem. Soc. 2005, 127, 7857e7870; (e) Yang, H.; Gao, H.; Angelici, R. J.
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thal, U.; Krossing, I. Tetrahedron Lett. 2007, 48, 8900e8903; (h) Aizenberg, M.;
Milstein, D. Science 1994, 265, 359e361.
tensity, %) 150 (M ,13),132 (25),117 (63),105 (100), 91 (29), 77 (11).
4
d
.3.5. 3-Phenylpropan-1-ol (21).24 Light-yellow liquid. 1H NMR:
1.28 (s, 1H), 1.89e1.96 (m, 2H), 2.74 (t, J¼7.7 Hz, 2H), 3.71 (t,
13
J¼6.4 Hz, 2H), 7.20e7.43 (m, 5H). C NMR:
d
32.1, 34.2, 62.3, 125.9,
þ
128.4, 128.4, 141.8. MS (EI) m/z (relative intensity, %) 136 (M , 25),
117 (100), 91 (65), 77 (11).
4
.4. Deuterium-labeling experiments
7. Schirok, H.; Paulsen, H.; Kroh, W.; Chen, G.; Gao, P. Org. Process Res. Dev. 2010,
1
4, 168e173.
. (a) Fuchibe, K.; Kaneko, T.; Mori, K.; Akiyama, T. Angew. Chem., Int. Ed. 2009, 48,
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8
4
.4.1. 2,2-Deuterio-2-(phenylthio)-ethanol (7). Compound 7 was
8
1
prepared by the same procedure as used for 6 with the reductant
lithium aluminum deuteride (LiAlD
1
4
). Light-yellow liquid. H NMR:
1
d
2.00 (s, 1H), 3.14 (t, J¼5.9 Hz, 0.2H), 3.76 (s, 2H), 7.23e7.43 (m, 5H).
1
3
2008, 3, 261e271; (f) Fuchibe, K.; Akiyama, T. Synlett 2004, 1282e1284.
. (a) O’Hagan, D. Chem. Soc. Rev. 2008, 37, 308e319; (b) Blanksby, S. J.; Ellison, G.
B. Acc. Chem. Res. 2003, 36, 255e263.
C NMR:
GCeMS: m/z¼156 (91), 125 (100), 110 (48), 77 (11). HRMS calcd for
OS: 156.0578, found 156.0570.
d
29.7 (t, J¼33.9 Hz), 60.2, 126.7, 129.1, 130.3, 134.8.
9
1
0. Wu, J.; Cao, S.; Liu, N.; Shen, L.; Yu, J.; Zhang, J.; Li, H.; Qian, X. Org. Biomol. Chem.
010, 8, 2386e2391.
1. (a) Johnson, J. E.; Blizzard, R. H.; Carhart, H. W. J. Am. Chem. Soc. 1948, 70,
3664e3665; (b) Krishnamurthy, S.; Brown, H. C. J. Org. Chem. 1982, 47, 276e280.
8 8 2
C H D
2
1
Acknowledgements
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We are grateful for financial supports from the National Natural
Science Foundation of China (Grant No. 21072057), the National
Basic Research Program of China (973 Program, 2010CB126101),
Shanghai Foundation of Science of Technology (09391911800), and
the Shanghai Leading Academic Discipline Project (B507).
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1
3
1
Supplementary data
2
1
4
1
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