G
A. Ortega-Martínez et al.
Paper
Synthesis
1,3-Dimethyl-3-(3-oxo-1,3-diphenylpropyl)indolin-2-one (9ah,
major diasteroisomer)
(4) (a) Jia, Y.-X.; Kündig, E. P. Angew. Chem. Int. Ed. 2009, 48, 1636.
(b) Perry, A.; Taylor, R. J. K. Chem. Commun. 2009, 3249.
(c) Ghosh, S.; De, S.; Kakde, B. N.; Bhunia, S.; Adhikary, A.; Bisai,
A. Org. Lett. 2012, 14, 5864.
Yield: 54 mg (97%); colorless oil.
1H NMR (300 MHz): δ = 7.98–7.87 (m, 2 H), 7.52 (m, 1 H), 7.48–7.35
(m, 2 H), 7.17 (m, 2 H), 7.07–6.97 (m, 6 H), 6.59 (d, J = 7.7 Hz, 1 H),
3.97 (dd, J = 8.1, 5.8 Hz, 1 H), 3.69–3.63 (m, 2 H), 3.05 (s, 3 H), 1.43 (s,
3 H).
13C NMR (101 MHz): δ = 198.9, 179.9, 142.9, 139.5, 137.2, 133.3,
133.1, 129.0, 128.6, 128.3, 127.9, 127.5, 126.8, 123.8, 122.4, 107.8,
51.6, 48.1, 38.4, 26.0, 22.1.
(5) (a) Tian, X.; Jiang, K.; Peng, J.; Du, W.; Chen, Y.-C. Org. Lett. 2008,
10, 3583. (b) He, R.; Ding, C.; Maruoka, K. Angew. Chem. Int. Ed.
2009, 48, 4559. (c) Cheng, L.; Liu, L.; Jia, H.; Wang, D.; Chen, Y.-J.
J. Org. Chem. 2009, 74, 4650. (d) Wu, X.; Liu, Q.; Liu, Y.; Wang, Q.;
Zhang, Y.; Chen, J.; Cao, W.; Zhao, G. Adv. Synth. Catal. 2013, 355,
2701. (e) Wei, Y.; Wen, S.; Liu, Z.; Wu, X.; Zheng, B.; Ye, J. Org.
Lett. 2015, 17, 2732. (f) Mechler, M.; Peters, R. Angew. Chem. Int.
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Chem. Int. Ed. 2016, 55, 4798. (h) Ohmatsu, K.; Kikoyama, M.;
Ooi, T. J. Am. Chem. Soc. 2011, 133, 1307. (i) Zhu, Q.; Lu, Y.
Angew. Chem. Int. Ed. 2010, 49, 7753. (j) Peng, J.; Huang, X.; Cui,
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Barbas, C. F. III. J. Am. Chem. Soc. 2009, 131, 8758. (l) Jiang, K.;
Peng, J.; Cui, H.-L.; Chen, Y.-C. Chem. Commun. 2009, 3955.
(m) Li, X.; Xi, Z.-G.; Luo, S.; Cheng, J.-P. Org. Biomol. Chem. 2010,
8, 77. (n) Wang, L.-L.; Peng, L.; Bai, J.-F.; Huang, Q.-C.; Xu, X.-Y.;
Wang, L.-X. Chem. Commun. 2010, 46, 8064. (o) Trost, B. M.;
Czabaniuk, L. C. J. Am. Chem. Soc. 2010, 132, 15534. (p) Trost, B.
M.; Frederiksen, M. U. Angew. Chem. Int. Ed. 2005, 44, 308.
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J.; Tunge, J. A. Chem. Rev. 2011, 111, 1846.
LRMS (EI): m/z = 369 (5) [M]+, 209 (17), 208 (16), 207 (25), 161 (69),
160 (13), 105 (100), 77 (27).
HRMS (EI): m/z calcd. for C25H23NO2: 369.1729; found: 369.1723.
Funding Information
We gratefully acknowledge financial support from the Spanish Minis-
terio de Ciencia e Innovación (MICINN) (projects CTQ2010-20387 and
Consolider Ingenio 2010, CSD2007-00006), the Spanish Ministerio de
Economía y Competitividad (MINECO) (projects CTQ2013-43446-P
and CTQ2014-51912-REDC), the Spanish Ministerio de Economía, In-
dustria y Competitividad, Agencia Estatal de Investigación (AEI) and
Fondo Europeo de Desarrollo Regional (FEDER, EU) (projects
CTQ2016-76782-P and CTQ2016-81797-REDC), the Generalitat Va-
lenciana (PROMETEO2009/039 and PROMETEOII/ 2014/017) and the
University of Alicante. A.O.-M. thanks MINECO for a predoctoral fel-
(7) Linton, E. C.; Kozlowski, M. C. J. Am. Chem. Soc. 2008, 130, 16162.
(8) Kumar, N.; Das, M. K.; Ghosh, S.; Bisai, A. Chem. Commun. 2017,
53, 2170.
(9) (a) Grenning, A. J.; Tunge, J. A. Angew. Chem. Int. Ed. 2011, 50,
1688. (b) Grenning, A. J.; Tunge, J. A. J. Am. Chem. Soc. 2011, 133,
14785.
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(10) For a review, see: Mei, H.; Xie, C.; Aceña, J. L.; Soloshonok, V. A.;
Röschenthaler, G.-V.; Han, J. Eur. J. Org. Chem. 2015, 6401.
(11) (a) Xie, C.; Zhang, L.; Sha, W.; Soloshonok, V. A.; Han, J.; Pan, Y.
Org. Lett. 2016, 18, 3270. (b) A very similar reaction principle
was employed but using harsher conditions, see: Reisch, J.;
Muller, M.; Labitzke, H. Arch. Pharm. 1984, 317, 639.
(12) Jha, M.; Chou, T.-Y.; Blunt, B. Tetrahedron Lett. 2011, 67, 982.
(13) Zhang, Q. B.; Jia, W. L.; Ban, Y. L.; Zheng, Y.; Liu, Q.; Wu, L. Z.
Chem. Eur. J. 2016, 22, 2595.
Supporting Information
1
Copies of H and 13C NMR spectra of new products.Supporting infor-
0036-1590880.
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References
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© Georg Thieme Verlag Stuttgart · New York — Synthesis 2017, 49, A–H