J. Ji et al. / Tetrahedron Letters 53 (2012) 182–185
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this article can be found, in the online version, at doi:10.1016/
OBn
O
CHO
InBr3, 40oC
InBr3, 25oC
O
O
+
+
N.R.
N.R.
O
O2N
MeO
MeO
3a
O
References and notes
9a
OBn
1. (a) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic
Synthesis with Diazo Compounds; John Wiley and Sons: New York, 1998; (b)
Zhang, Z.; Wang, J. Tetrahedron 2008, 64, 6577; (c) Zhang, Y.; Wang, J. Chem.
Commun. 2009, 5350; (d) Lian, Y.; Miller, L. C.; Born, S.; Sarpong, R.; Davies, H. M.
L. J. Am. Chem. Soc. 2010, 132, 12422; (e) Schwartz, B. D.; Denton, J. R.; Lian, Y.;
Davies, H. M. L.; Williams, C. M. J. Am. Chem. Soc. 2009, 131, 8329.
2. (a) Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev. 2010, 110, 704; (b)
Davies, H. M. L.; Morton, D. Chem. Soc. Rev. 2011, 40, 1857; (c) Liu, B.; Zhu, S.-F.;
Zhang, W.; Chen, C.; Zhou, Q.-L. J. Am. Chem. Soc. 2007, 129, 5834; (d) Lee, E. C.;
Fu, G. C. J. Am. Chem. Soc. 2007, 129, 12066; (e) Flynn, C. J.; Elcoate, C. J.;
Lawrence, S. E.; Maguire, A. R. J. Am. Chem. Soc. 2010, 132, 1184.
O
O
O
9a
4a
OMe
O
O
N2
CHO
O
InBr3
+
O
O2N
MeO
O
3a
1a
MeO
3. (a) Peng, C.; Wang, Y.; Wang, J. J. Am. Chem. Soc. 2008, 130, 1566; (b) Ni, Y.;
Montgomery, J. J. Am. Chem. Soc. 2006, 128, 2609; (c) Che, C.-M.; Huang, J.-S.; Lee,
F.-W.; Li, Y.; Lai, T.-S.; Kwong, H.-L.; Teng, P.-F.; Lee, W.-S.; Lo, W.-C.; Peng, S.-M.;
Zhou, Z.-Y. J. Am. Chem. Soc. 2001, 123, 4119; (d) Zhu, S.; Perman, J. A.; Zhang, X.
P. Angew. Chem., Int. Ed. 2008, 47, 8460; (e) Wang, S. R.; Zhu, C.-Y.; Sun, X.-L.;
Tang, Y. J. Am. Chem. Soc. 2009, 131, 4192; (f) Zhu, S.-F.; Cai, Y.; Mao, H.-X.; Xie, J.-
H.; Zhou, Q.-L. Nat. Chem. 2010, 2, 546.
Scheme 3. Control reactions.
Acknowledgments
4. (a) Pellicciari, R.; Natalini, B.; Sadeghpour, B. M.; Marinozzi, M.; Snyder, J. P.;
Williamson, B. L.; Kuethe, J. T.; Padwa, A. J. Am. Chem. Soc. 1996, 118, 1; (b)
Draghici, C.; Brewer, M. J. Am. Chem. Soc. 2008, 130, 3766; (c) Muthusamy, S.;
Babu, S. A.; Gunanathan, C. Tetrahedron Lett. 2002, 43, 3133; (d) Yadav, J. S.;
Reddy, B. V. S.; Satheesh, G. Tetrahedron Lett. 2003, 44, 8331; (e) Smith, A. B.;
Dieter, R. K. J. Am. Chem. Soc. 1981, 103, 2017.
5. (a) Hu, W.; Xu, X.; Zhou, J.; Liu, W.-J.; Huang, H.; Hu, J.; Yang, L.; Gong, L.-Z. J. Am.
Chem. Soc. 2008, 130, 7782; (b) Huang, H.; Guo, X.; Hu, W. Angew. Chem., Int. Ed.
2007, 46, 1337; (c) Lu, Chong-D.; Liu, H.; Chen, Z.-Y.; Hu, W.-H.; Mi, A.-Q. Org.
Lett. 2005, 7, 83; (d) Yue, Y.; Guo, X.; Chen, Z.; Yang, L.; Hu, W. Tetrahedron Lett.
2008, 49, 6862; (e) Guo, X.; Huang, H.; Yang, L.; Hu, W. Org. Lett. 2007, 9, 4721.
6. Ji, J.; Zhang, X.; Zhu, Y.; Qian, Y.; Zhou, J.; Yang, L.; Hu, W. J. Org. Chem. 2011, 76,
5821.
We wish to thank the National Science Foundation of China
(20932003, 21002033) and the MOST of China (2011CB808600)
for financial support and Shanghai (09JC1404901, 10XD1401700)
for sponsorship.
Supplementary data
Supplementary data (complete experimental details and spec-
troscopic characterization of all new compounds) associated with