PAPER
Enantioselective Friedel–Crafts Alkylation of Indoles
3999
1H NMR (400 MHz, CDCl3): d = 8.54 (br s, 1 H), 8.41 (s, 1 H), 8.05
(d, J = 9.2 Hz, 1 H), 7.19–7.36 (m, 7 H), 4.44 (t, J = 7.8 Hz, 1 H),
3.64–3.71 (m, 2 H), 2.42–2.48 (m, 1 H), 2.26–2.34 (m, 1 H), 1.64
(br s, 1 H).
13C NMR (100 MHz, CDCl3): d = 38.5, 38.8, 60.8, 111.0, 116.8,
117.9, 122.6, 123.9, 126.3, 126.7, 127.7, 128.7, 139.5, 141.5, 143.6.
9, 1403. (c) Tang, H.-Y.; Lu, A.-D.; Zhou, Z.-H.; Zhao, G.-
F.; He, L.-N.; Tang, C.-C. Eur. J. Org. Chem. 2008, 1406.
(9) (a) Wang, Y.-Q.; Song, J.; Hong, R.; Li, H.; Deng, L. J. Am.
Chem. Soc. 2006, 128, 8156. (b) Kang, Q.; Zhao, Z.-A.;
You, S.-L. J. Am. Chem. Soc. 2007, 129, 1484.
(c) Rowland, G. B.; Rowland, E. B.; Liang, Y.; Perman, J.
A.; Antilla, J. C. Org. Lett. 2007, 9, 2609. (d) Wanner, M.
J.; Hauwert, P.; Schoemaker, H. E.; de Gelder, R.;
van Maarseveen, J. H.; Hiemstra, H. Eur. J. Org. Chem.
2008, 180.
EI-MS: m/z = 296 [M+].
Anal. Calcd for C17H16N2O3: C, 68.91; H, 5.44; N, 9.45. Found: C,
68.82; H, 5.41; N, 9.46.
(10) Török, B.; Abid, M.; London, G.; Esquibel, J.; Török, M.;
Mhadgut, S. C.; Yan, P.; Prakash, G. K. S. Angew. Chem.
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Acknowledgment
(11) Terada, M.; Sorimachi, K. J. Am. Chem. Soc. 2007, 129, 292.
(12) For the first reports on the use of diarylprolinol silyl ethers,
see: (a) Marigo, M.; Wabnitz, T. C.; Fielenbach, D.;
Jørgensen, K. A. Angew. Chem. Int. Ed. 2005, 44, 794.
(b) Marigo, M.; Fielenbach, D.; Braunton, A.; Kjasgaard, A.;
Jørgensen, K. A. Angew. Chem. Int. Ed. 2005, 44, 3703.
(c) Hayashi, Y.; Gotoh, H.; Hayashi, T.; Shoji, M. Angew.
Chem. Int. Ed. 2005, 44, 4212.
This work was financially supported by the Specialized Research
Fund for the Doctoral Program of Higher Education of China
(20060335036) and Zhejiang Provincial Natural Science Founda-
tion of China under Grant No. Y406049.
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Synthesis 2009, No. 23, 3994–4000 © Thieme Stuttgart · New York