The Journal of Organic Chemistry
NOTE
2H), 3.32 (dd, J = 16.5, 5.0 Hz, 1H), 2.91 (dd, J = 16.5, 8.0 Hz, 1H); 13
C
Engle, K. M; Wang, D.-H.; Yu, J.-Q Angew. Chem., Int. Ed. 2009,
48, 5094.
(2) (a) Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Commun. 2010, 46, 677.
(b) Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem., Int. Ed. 2009,
48, 9792.
NMR (125 MHz, CDCl3) δ 169.6, 166.2, 144.8, 144.3, 143.5, 140.6,
136.0, 135.3, 130.6, 128.6, 128.5, 128.43, 128.41, 128.3, 128.2, 127.8,
127.7, 125.7, 124.8, 120.1, 99.5, 67.0, 66.5, 58.8, 38.8; HRMS (ESI) calcd
for [C29H24N2O4 + H]+ 465.1811, found 465.1814.
Compound 4c: yellow solid; yield 72%; 1H NMR (500 MHz, CDCl3)
δ 8.07 (d, J = 16.0 Hz, 1H), 7.68 (d, J = 2.0 Hz, 1H), 7.63 (d, J = 8.0 Hz,
1H), 7.48 (d, J = 7.5 Hz, 1H), 7.32 (t, J = 7.5 Hz, 1H), 6.54 (d, J = 16.0
Hz, 1H), 6.50 (d, J = 1.5 Hz, 1H), 5.55À5.57 (m, 1H), 4.25 (t, J = 6.5 Hz,
2H), 4.14 (t, J = 6.5 Hz, 2H), 3.28 (dd, J = 16.5, 5.0 Hz, 1H), 2.84 (dd, J =
16.5, 8.0 Hz, 1H), 1.69À1.75 (m, 2H), 1.54À1.60 (m, 2H), 1.43À1.50
(m, 2H), 1.29À1.36 (m, 2H), 0.98 (t, J = 7.5 Hz, 3H), 0.90 (t, J = 7.5 Hz,
3H); 13C NMR (125 MHz, CDCl3) δ 169.9, 166.5, 145.0, 144.2, 143.5,
140.0, 130.5, 128.0, 127.8, 125.7, 124.7, 120.5, 99.4, 65.0, 64.6, 58.8, 38.8,
30.8, 30.5, 19.2, 19.0, 13.7, 13.6; HRMS (ESI) calcd for [C23H28N2O4 +H]+
397.2127, found 397.2122.
(3) (a) Elguero, J.; Goya, P.; Jagerovic, N.; Silva, A. M. S. In Targets in
Heterocyclic Systems; Attanasi, O. A., Spinelli, D., Eds.; Italian Society of
Chemistry: Roma, 2002; Vol. 6, p 52. (b) Zhang, J.; Didierlaurent, S.;
Fortin, M.; Lefrancois, D.; Uridat, E.; Vevert, J. P. Bioorg. Med. Chem.
Lett. 2000, 10, 1351.
(4) (a) Jothibasu, R.; Huynh, H. V. Chem. Commun. 2010, 46, 2986.
For a recent review, see: (b) Schuster, O.; Yang, L. R.; Raubenheimer,
H. G.; Albrecht, M. Chem. Rev. 2009, 109, 3445.
(5) For recent reviews see: (a) Colby, D. A.; Bergman, R. G.; Ellman,
J. A. Chem. Rev. 2010, 110, 624. (b) Satoh, T.; Miura, M. Chem. Eur. J.
2010, 37, 11212. For individual reports, see: (c) Rakshit, S.; Grohmann,
C.; Besset, T.; Glorius, F. J. Am. Chem. Soc. 2011, 133, 2350. (d)
Patureau, F. W.; Besset, T.; Glorius, F. Angew. Chem., Int. Ed. 2011,
50, 1064. (e) Li, Y.; Li, B.-J.; Wang, W.-H.; Huang, W.-P.; Zhang, X.-S.;
Chen, K.; Shi, Z.-J. Angew. Chem., Int. Ed. 2011, 50, 2115. (f) Mochida,
S.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2010, 12, 5776.
(6) (a) Patureau, F. W.; Besset, T.; Kuhl, N.; Glorius, F. J. Am. Chem.
Soc. 2011, 133, 2154. (b) Stuart, D. R.; Alsabeh, P.; Kuhn, M.; Fagnou, K.
J. Am. Chem. Soc. 2010, 132, 18326. (c) Morimoto, K.; Hirano, K.; Satoh,
T.; Miura, M. Org. Lett. 2010, 12, 2068. (d) Fukutani, T.; Hirano, K.;
Satoh, T.; Miura, M. Org. Lett. 2009, 11, 5198. (e) Li, L.; Brennessel,
W. W.; Jones, W. D. J. Am. Chem. Soc. 2008, 130, 12414.
(7) (a) Chen, J.; Song, G.; Pan, C.-L.; Li, X. Org. Lett. 2010, 12, 5426.
(b) Wang, F.; Song, G.; Li, X. Org. Lett. 2010, 12, 5430. (c) Song, G.;
Chen, D.; Pan, C.-L.; Crabtree, R. H.; Li, X. J. Org. Chem. 2010, 75, 7487.
(d) Su, Y.; Zhao, M.; Han, K.; Song, G.; Li, X. Org. Lett. 2010, 12, 5462.
(e) Zhang, X. P.; Chen, D.; Zhao, M.; Zhao, J.; Jia, A. Q.; Li, X. Adv.
Synth. Catal. 2011, 353, 719. (f) Wang, F.; Song, G.; Du, Z.; Li, X. J. Org.
Chem. 2011, 76, 2926.
Compound 4d: yellow solid; yield 62%; 1H NMR (500 MHz, CDCl3)
δ 8.08 (d, J = 16 Hz, 1H), 7.66 (d, J = 2.0 Hz, 1H), 7.32À7.46 (m, 11H),
7.19 (s, 1H), 6.57 (d, J = 16 Hz, 1H), 6.42 (d, J = 2.0 Hz, 1H),5.52À5.55
(m, 1H), 5.30 (s, 2H), 5.20 (s, 2H), 3.32 (dd, J = 16.5, 5.0 Hz, 1H), 2.89
(dd, J = 16.5, 8.0 Hz, 1H), 2.35 (s, 3H); 13C NMR (125 MHz, CDCl3) δ
169.7, 166.3, 145.1, 144.1, 143.6, 140.8, 138.0, 136.0, 135.4, 128.7, 128.6,
128.5, 128.4, 128.3, 128.2, 128.1, 127.5, 126.2, 125.8, 119.8, 98.9, 66.9,
66.5, 58.6, 38.9, 21.5; HRMS (ESI) calcd for [C30H26N2O4 + H]+
479.1971, found 479.1964.
Compound 4e: yellow solid; yield 51%; 1H NMR (500 MHz, CDCl3)
δ 8.00 (d, J = 16 Hz, 1H), 7.67 (d, J = 2.0 Hz, 1H), 7.58, (d, J = 1.5 Hz,
1H), 7.28À7.45 (m, 11H), 6.57 (d, J = 16 Hz, 1H), 6.46 (d, J = 2.0 Hz,
1H), 5.54À5.56 (m, 1H), 5.30 (s, 2H), 5.20 (s, 2H), 3.35 (dd, J = 17.5,
5.0 Hz, 1 H), 2.90 (dd, J = 17, 8.0 Hz, 1 H); 13C NMR (125 MHz,
CDCl3) δ 169.4, 165.9, 146.4, 144.4, 142.6, 139.3, 135.8, 135.2, 133.8,
129.0, 128.8, 128.6, 128.53, 128.50, 128.4, 128.3, 128.2, 125.7, 125.3, 121.3,
99.6, 67.1, 66.7, 58.6, 38.5; HRMS (ESI) calcd for [C29H23ClN2O4 + H]+
499.1424, found 499.1418.
(8) (a) Guimond, N.; Fagnou, K. J. Am. Chem. Soc. 2009, 131, 12050.
(b) Fukutani, T.; Umeda, N.; Hirano, K.; Satoh, T.; Miura, M. Chem.
Commun. 2009, 44, 5141.
1
Compound 4f: light yellow solid; yield 51%; H NMR (500 MHz,
(9) (a) Hyster, T. K.; Rovis, T. J. Am. Chem. Soc. 2010, 132, 10565.
(b) Mochida, S.; Umeda, N.; Hirano, K.; Satoh, T.; Miura, M. Chem. Lett.
2010, 39, 744.
(10) Stuart, D. R.; Bertrand-Laperle, M.; Burgess, K. M. N.; Fagnou,
K. J. Am. Chem. Soc. 2008, 130, 16474.
(11) (a) Ueura, K.; Satoh, T.; Miura, M. Org. Lett. 2007, 9, 1407. (b)
Ueura, K.; Satoh, T.; Miura, M. J. Org. Chem. 2007, 72, 5362.
(12) Mochida, S.; Shimizu, M.; Hirano, K.; Satoh, T.; Miura, M.
Chem. Asian J. 2010, 5, 847.
CDCl3) δ 7.75 (s, 1H), 7.44À7.33 (m, 7H), 7.28À7.24 (m, 1H), 6.62,
(s, 1H), 5.67 (dd, J = 9.5, 7.0 Hz, 1 H), 5.27 (s, 2H), 3.40 (dd, J = 20.5,
6.5 Hz, 1 H), 2.95 (dd, J = 20.5, 10 Hz, 1 H); 13C NMR (125 MHz,
CDCl3) δ 169.6, 145.6, 144.0, 135.3, 130.9, 129.3, 129.1, 128.8, 128.6,
128.52, 128.50, 128.4, 127.0, 99.4, 67.0, 59.2, 38.8; HRMS (ESI) calcd
for [C19H15ClN2O2 + H]+ 339.0901, found 339.0908.
’ ASSOCIATED CONTENT
(13) Rakshit, S.; Patureau, F. W.; Glorius, F. J. Am. Chem. Soc. 2010,
132, 9585.
(14) Hyster, T. K.; Rovis, T. Chem. Sci. 2011, 2, 1606.
(15) (a) Chen, J.; Pang, Q.; Sun, Y.; Li, X. J. Org. Chem. 2011,
76, 3523. (b) Gong, T. J.; Xiao, B.; Liu, Z. J.; Wan, J.; Xu, J.; Luo, D. F.;
Fu, Y.; Liu, L. Org. Lett. 2011, 13, 3235.
S
Supporting Information. Figures giving NMR spectra
b
and characterization data for new products. This material is
’ AUTHOR INFORMATION
(16) Abunada, N. M.; Hassaneen, H. H.; Kandile, N. G.; Miqdad,
O. A. Molecules 2008, 13, 1501.
Corresponding Author
*E-mail: xwli@dicp.ac.cn.
(17) (a) Umeda, N.; Hirano, K.; Satoh, T.; Shibata, N.; Sato, H.;
Miura, M. J. Org. Chem. 2011, 76, 13. (b) Umeda, N.; Hirano, K.; Satoh,
T.; Miura, M. J. Org. Chem. 2009, 74, 7094. (c) Umeda, N.; Tsurugi, H.;
Satoh, T.; Miura, M. Angew. Chem., Int. Ed. 2008, 47, 4019.
(18) (a) Wasa, M.; Engle, K. M.; Yu, J.-Q. J. Am. Chem. Soc. 2010,
132, 3680. (b) Mochida, S.; Hirano, K.; Satoh, T.; Miura, M. J. Org.
Chem. 2009, 74, 6295.
(19) (a) Pleier, A.-K.; Glas, H.; Grosche, M.; Sirsch, P.; Thiel, W. R.
Synthesis 2001, 55. (b) Mitkidou, S.; Stephanidou-Stephanatou, J.
Tetrahedron Lett. 1990, 31, 5197.
’ ACKNOWLEDGMENT
This work was supported by the Dalian Institute of Chemical
Physics, Chinese Academy of Sciences. We thank Dr. Guoyong
Song for helpful discussions.
’ REFERENCES
(1) (a) Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215. (b)
Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147. (c) Xu, L.-M.;
Li, B.-J.; Yang, Z.; Shi, Z.-J. Chem. Soc. Rev. 2010, 39, 712. (d) Chen, X.;
8536
dx.doi.org/10.1021/jo201530r |J. Org. Chem. 2011, 76, 8530–8536