Y.-S. Feng et al. / Tetrahedron 68 (2012) 2113e2120
2119
(t, J¼7.2 Hz, 3H). 13C NMR (75 MHz, CDCl3, 293 K, TMS):
d
172.33,
7.70 (d, J¼8.7 Hz, 3H), 7.41 (dd, J¼8.4, 1.8 Hz, 1H), 7.12 (dt, J¼7.5,
144.88, 131.39, 127.42, 117.70, 110.05, 60.15, 44.61, 17.31, 13.04. MS
found: 203.09.
2.4 Hz, 2H), 3.91 (s, 3H), 3.89e3.82 (m, 1H), 1.58 (d, J¼7.2 Hz, 3H). 13
C
NMR (75 MHz, CDCl3, 293 K, TMS):
d 180.25, 157.73, 134.91, 133.83,
129.30, 128.92, 127.24, 126.19, 126.14, 119.04, 105.64, 55.31, 45.22,
18.14. MS found: 230.09.
4.2.37. Ethyl 2-(3-cyanophenyl)propanoate (2k). Following general
procedure, a white liquid was obtained. 1H NMR (300 MHz, CDCl3,
293 K, TMS):
(m, 2H), 3.67 (q, J¼7.2 Hz,1H),1.44 (d, J¼7.2 Hz, 3H),1.14 (t, J¼7.2 Hz,
3H). 13C NMR (75 MHz, CDCl3, 293 K, TMS):
172.44, 140.98, 131.14,
130.26, 129.84, 128.40, 117.68, 111.67, 60.15, 44.12, 17.36, 13.06.
HRMS calcd for C12H13NO2 203.0946; found: 203.10202.
d 7.57e7.44 (m, 3H), 7.40e7.32 (m, 1H), 4.12e3.99
Acknowledgements
d
We gratefully acknowledge financial support from the National
Natural Science Foundation of China (Nos. 20802015, 21072040,
21071040).
4.2.38. Ethyl 2-(4-(tosyloxy)phenyl)propanoate (2l). Following
Supplementary data
general procedure, a white liquid was obtained. 1H NMR (300 MHz,
CDCl3, 293 K, TMS):
d
7.62 (d, J¼8.4 Hz, 2H), 7.22 (d, J¼8.4 Hz, 2H),
Supplementary data related to this article can be found online
InChIKeys of the most important compounds described in this
article.
7.14 (d, J¼8.7 Hz, 2H), 6.85 (d, J¼8.7 Hz, 2H), 4.09e3.96 (m, 2H), 3.59
(q, J¼7.2 Hz, 1H), 2.36 (s, 3H), 1.37 (d, J¼7.2 Hz, 3H), 1.11 (t, J¼7.2 Hz,
3H). 13C NMR (75 MHz, CDCl3, 293 K, TMS):
d 173.01, 147.54, 144.37,
138.55, 131.40, 128.75, 127.70, 127.43, 121.37, 59.82, 43.87, 20.66,
17.48 (s), 13.03. HRMS calcd for C18H20O5S 348.1031; found:
348.1109.
References and notes
1. (a) Goossen, L. J.; Rodriguez, N.; Goossen, K. Angew. Chem., Int. Ed. 2008, 47,
3100; (b) Goossen, L. J.; Collet, F.; Goossen, K. Isr. J. Chem. 2010, 50, 617; (c)
Weaver, J. D.; Recio, A., III; Grenning, A. J.; Tunge, J. A. Chem. Rev. 2011, 111, 1846;
(d) Rodríguez, N.; Goossen, L. J. Chem. Soc. Rev. 2011, 40, 5030; (e) Shang, R.; Liu,
L. Sci. China: Chem. 2011, 54, 1670.
2. (a) Rayabarapu, D. K.; Tunge, J. A. J. Am. Chem. Soc. 2005, 127, 13510; (b) Burger,
E. C.; Tunge, J. A. J. Am. Chem. Soc. 2006, 128, 10002; (c) Waetzig, S. R.; Raya-
barapu, D. K.; Weaver, J. D.; Tunge, J. A. Angew. Chem., Int. Ed. 2006, 45, 4977; (d)
Waetzig, S. R.; Tunge, J. A. J. Am. Chem. Soc. 2007, 129, 4138; (e) Waetzig, S. R.;
Tunge, J. A. J. Am. Chem. Soc. 2007, 129, 14860; (f) Torregrosa, R. R. P.; Ariyar-
athna, Y.; Chattopadhyay, K.; Tunge, J. A. J. Am. Chem. Soc. 2010, 132, 9280; (g)
Weaver, J. D.; Ka, B. J.; Morris, D. K.; Thompson, W.; Tunge, J. A. J. Am. Chem. Soc.
2010, 132, 12179; (h) Jana, R.; Partridge, J. J.; Tunge, J. A. Angew. Chem., Int. Ed.
2011, 50, 5157.
4.2.39. Ethyl 2-(4-(methylthio)phenyl)butanoate (2m). Following
general procedure, a yellow liquid was obtained. 1H NMR (300 MHz,
CDCl3, 293 K, TMS):
d
7.20e7.05 (m, 4H), 4.04 (dq, J¼6.0, 3.6 Hz, 2H),
3.31 (t, J¼7.8 Hz, 1H), 2.39 (s, 3H), 2.09e1.90 (m, 1H), 1.80e1.60 (m,
1H), 1.13 (t, J¼7.2 Hz, 3H), 0.81 (t, J¼7.5 Hz, 3H). 13C NMR (75 MHz,
CDCl3, 293 K, TMS):
d 172.94, 136.08, 135.12, 127.42, 125.78, 59.61,
51.98, 25.70, 14.87, 13.13, 11.09. HRMS calcd for C13H18O2S 238.1028;
found: 238.1101.
4.2.40. Ethyl 2-(4-methoxyphenyl)-2-methylpropanoate
3. (a) Trost, B. M.; Xu, J.; Schmidt, T. J. Am. Chem. Soc. 2008, 130, 11852; (b) Trost, B.
M.; Xu, J.; Schmidt, T. J. Am. Chem. Soc. 2009, 131, 18343.
4. Mohr, J. T.; Nishimata, T.; Behenna, D. C.; Stoltz, B. M. J. Am. Chem. Soc. 2006, 128,
11348.
(2n). Following general procedure, a white liquid was obtained.
1H NMR (300 MHz, CDCl3, 293 K, TMS):
d
7.30e7.24 (m, 2H),
6.90e6.81 (m, 2H), 4.11 (q, J¼7.2 Hz, 2H), 3.79 (s, 3H), 1.55 (s, 6H),
5. (a) Goossen, L. J.; Deng, G.; Levy, L. M. Science 2006, 313, 662; (b) Goossen, L. J.;
Rodriguez, N.; Melzer, B.; Linder, C.; Deng, G.; Levy, L. M. J. Am. Chem. Soc. 2007,
129, 4824; (e) Goossen, L. J.; Rudolphi, F.; Oppel, C.; Rodriguez, N. Angew. Chem.,
Int. Ed. 2008, 47, 3043; (f) Goossen, L. J.; Rodriguez, N.; Lange, P.; Linder, C.
Angew. Chem., Int. Ed. 2010, 49, 1111; (g) Lange, P. P.; Goossen, L. J.; Podmore, P.;
Underwood, T.; Sciammetta, N. Chem. Commun. 2011, 3628.
6. (a) Myers, A. G.; Tanaka, D.; Mannion, M. R. J. Am. Chem. Soc. 2002, 124, 11250;
(b) Tanaka, D.; Myers, A. G. Org. Lett. 2004, 6, 433; (c) Tanaka, D.; Romeril, S. P.;
Myers, A. G. J. Am. Chem. Soc. 2005, 127, 10323.
7. (a) Forgione, P.; Brochu, M. C.; St-Onge, M.; Thesen, K. H.; Bailey, M. D.;
Bilodeau, F. J. Am. Chem. Soc. 2006, 128, 11350; (b) Bilodeau, F.; Brochu, M. C.;
Guimond, N.; Thesen, K. H.; Forgione, P. J. Org. Chem. 2010, 75, 1550.
8. (a) Shang, R.; Fu, Y.; Li, J. B.; Zhang, S. L.; Guo, Q. X.; Liu, L. J. Am. Chem. Soc. 2009,
131, 5738; (b) Shang, R.; Fu, Y.; Wang, Y.; Xu, Q.; Yu, H.-Z.; Liu, L. Angew. Chem.,
Int. Ed. 2009, 48, 9350; (c) Shang, R.; Xu, Q.; Jiang, Y.-Y.; Wang, Y.; Liu, L. Org.
Lett. 2010, 12, 1000; (d) Zhang, S. L.; Fu, Y.; Shang, R.; Guo, Q. X.; Liu, L. J. Am.
Chem. Soc. 2010, 132, 638; (e) Dai, J.-J.; Liu, J.-H.; Luo, D.-F.; Liu, L. Chem. Com-
mun. 2011, 677.
9. (a) Maehara, A.; Tsurugi, H.; Satoh, T.; Miura, M. Org. Lett. 2008, 10, 1159; (b)
Yamashita, M.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2009, 11, 2337; (c)
Miyasaka, M.; Fukushima, A.; Satoh, T.; Hirano, K.; Miura, M. Chem.dEur. J.
2009, 15, 3674; (d) Miyasaka, M.; Hirano, K.; Satoh, T.; Miura, M. Adv. Synth.
Catal. 2009, 351, 2683; (e) Yamashita, M.; Hirano, K.; Satoh, T.; Miura, M. Chem.
Lett. 2010, 39, 68; (f) Yamashita, M.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett.
2010, 12, 592; (g) Yamashita, M.; Hirano, K.; Satoh, T.; Miura, M. Adv. Synth.
Catal. 2011, 353, 631.
1.18 (t, J¼7.2 Hz, 3H). 13C NMR (75 MHz, CDCl3, 293 K, TMS):
d
176.90, 158.18, 131.41, 126.76, 113.64, 60.72, 55.21, 45.71, 26.61,
14.06. HRMS calcd for C13H18O3 222.2802; found: 222.1174.
4.2.41. Ethyl 2-methyl-2-(4-(methylthio)phenyl)propanoate (2o).
Following general procedure, a yellow liquid was obtained. 1H
NMR (300 MHz, CDCl3, 293 K, TMS):
d 7.19e7.11 (m, 4H), 4.03
(q, J¼7.2 Hz, 2H), 2.39 (s, 3H), 1.48 (s, 6H), 1.10 (t, J¼7.2 Hz, 3H). 13C
NMR (75 MHz, CDCl3, 293 K, TMS): d 175.57, 140.81, 135.53, 125.67,
125.22, 59.81, 45.05, 25.44, 14.90, 13.03. HRMS calcd for C13H18O2S
238.1028; found: 238.0945.
4.2.42. Ethyl 2-(6-methoxynaphthalen-2-yl)propanoate (3a).32
Following general procedure, a white solid was obtained. 1H NMR
(300 MHz, CDCl3, 293 K, TMS):
d
7.65e7.49 (m, 3H), 7.31 (dd, J¼8.4,
1.5 Hz, 1H), 7.06e6.96 (m, 2H), 4.10e3.94 (m, 2H), 3.77 (s, 3H),
3.75e3.67 (m, 1H), 1.47 (d, J¼7.2 Hz, 3H), 1.09 (t, J¼7.2 Hz, 3H). 13C
NMR (75 MHz, CDCl3, 293 K, TMS): d 174.71, 157.66, 135.90, 133.72,
129.31, 128.99, 127.15, 126.28, 125.95, 118.98, 105.63, 60.76, 55.28,
45.53, 18.65, 14.17. MS found: 258.13.
10. (a) Bi, H.-P.; Zhao, L.; Liang, Y.-M.; Li, C.-J. Angew. Chem., Int. Ed. 2009, 48, 792;
(b) Bi, H.-P.; Chen, W.-W.; Liang, Y.-M.; Li, C.-J. Org. Lett. 2009, 11, 3246; (c)
Zhang, C.; Seidel, D. J. Am. Chem. Soc. 2010, 132, 1798; (d) Shang, R.; Yang, Z. W.;
Wang, Y.; Zhang, S.-L.; Liu, L. J. Am. Chem. Soc. 2010, 132, 14391; (e) Shang, R.; Ji,
D. S.; Chu, L.; Fu, Y.; Liu, L. Angew. Chem., Int. Ed. 2011, 50, 4470; (f) Yeung, P. Y.;
Chung, K. H.; Kwong, F. Y. Org. Lett. 2011, 13, 2912; (g) Shang, R.; Huang, Z.; Chu,
L.; Fu, Y.; Liu, L. Org. Lett. 2011, 13, 4240.
4.2.43. 2-(6-Methoxynaphthalen-2-yl)propanoic acid (4a). According
to the literature procedure, a 50 mL, two-necked, round-bottomed
flask was charged with ethyl 2-(6-methoxynaphthalen-2-yl)prop-
anoate (700 mg, 2.75 mmol) and ethanol (4 mL). Then, a solution of
sodium hydroxide (2.76 mmol) in ethanol (9 mL) was added slowly
over 5 min. The mixture was stirred at reflux for about 3 h. After
cooling the mixture to 0 ꢀC, the pH value was adjusted to 2 by adding
1 N hydrogen chloride. Standard extractive workup with ethyl ace-
tate (3ꢁ25 mL) gave the title product as a white solid (637 mg;
11. (a) Millard, A. A.; Rathke, M. W. J. Am. Chem. Soc. 1977, 99, 4833; (b) Lloyd-Jones,
G. C. Angew. Chem., Int. Ed. 2002, 41, 953; (c) Zeevaart, J. G.; Parkinson, C. J.;
Koning, C. B. D. Tetrahedron Lett. 2004, 45, 4261; (d) Ozdemir, I.; Yigit, M.;
C¸ etinkaya, E.; C¸ etinkaya, B. Tetrahedron Lett. 2004, 45, 5823.
12. Fors, B. P.; Buchwald, S. L. J. Am. Chem. Soc. 2009, 131, 12898.
13. Peng, Z. Y.; Wang, J. P.; Cheng, J. A.; Xie, X. M.; Zhang, Z. G. Tetrahedron 2010, 66,
8238.
€
ꢀ
yield¼97%). 1H NMR (300 MHz, CDCl3, 293 K, TMS):
d
10.03 (s, 1H),
14. Christian, R.; Gerhard, S.; Piotr, M. Collect. Czech. Chem. Commun. 1990, 55, 97.