ChemComm
Communication
P. H. Toy, Synthesis, 2008, 2307; ( f ) L.-W. Ye, J. Zhou and Y. Tang,
Chem. Soc. Rev., 2008, 37, 1140; (g) S. E. Denmark and G. L. Beutner,
Angew. Chem., 2008, 120, 1584 (Angew. Chem., Int. Ed., 2008, 47, 1560);
(h) C. E. Aroyan, A. Dermenci and S. J. Miller, Tetrahedron, 2009,
65, 4069; (i) B. J. Cowen and S. J. Miller, Chem. Soc. Rev., 2009, 38, 3102;
( j) A. Marinetti and A. Voituriez, Synlett, 2010, 174; (k) B. Kolesinska,
Cent. Eur. J. Chem., 2010, 1147.
5 C. Zhang and X. Lu, J. Org. Chem., 1995, 60, 2906.
6 (a) G. Zhu, Z. Chen, Q. Jiang, D. Xiao, P. Cao and X. Zhang, J. Am.
Chem. Soc., 1997, 119, 3836; (b) J. E. Wilson and G. C. Fu, Angew.
Chem., Int. Ed., 2006, 45, 1426; (c) X. Han, Y. Wang, F. Zhong and
Y. Lu, J. Am. Chem. Soc., 2011, 133, 1726; (d) F. Zhong, X. Han,
Y. Wang and Y. Lu, Angew. Chem., Int. Ed., 2011, 50, 7837; (e) X. Han,
F. Zhong, Y. Wang and Y. Lu, Angew. Chem., Int. Ed., 2012, 51, 767;
( f ) F. Zhong, J. Luo, G.-Y. Chen, X. Dou and Y. Lu, J. Am. Chem. Soc.,
2012, 134, 10222; (g) F. Zhong, X. Han, Y. Wang and Y. Lu, Chem.
Sci., 2012, 3, 1231; (h) F. Zhong, X. Dou, X. Han, W. Yao, Q. Zhu,
Y. Meng and Y. Lu, Angew. Chem., Int. Ed., 2013, 52, 943.
7 X. Meng, Y. Huang and R. Chen, Org. Lett., 2009, 11, 137.
8 Z. Lu, S. Zheng, X. Zhang and X. Lu, Org. Lett., 2008, 10, 3267.
9 X.-F. Zhu, C. E. Henry, J. Wang, T. Dudding and O. Kwon, Org. Lett.,
2005, 7, 1387–1390.
Scheme 3 Proposed mechanism.
annulation reactions and on performing asymmetric versions
of the annulation.
10 (a) T. Wang and S. Ye, Org. Lett., 2010, 12, 4168; (b) Q.-M. Zhang, L. Yang
and X. Tong, J. Am. Chem. Soc., 2010, 132, 2550; (c) S. Castellano,
H. D. G. Fiji, S. S. Kinderman, M. Watanabe, P. de Leon, F. Tamanoi and
O. Kwon, J. Am. Chem. Soc., 2007, 129, 5843; (d) Y. S. Tran and O. Kwon,
J. Am. Chem. Soc., 2007, 129, 12632; (e) R. P. Wurz and G. C. Fu, J. Am.
Chem. Soc., 2005, 127, 12234; ( f ) X.-F. Zhu, J. Lan and O. Kwon, J. Am.
Chem. Soc., 2003, 125, 4716.
11 S. Xu, L. Zhou, R. Ma, H. Song and Z. He, Org. Lett., 2010, 12, 544.
12 J. Tian and Z. He, Chem. Commun., 2013, 49, 2058.
13 H. Guo, Q. Xu and O. Kwon, J. Am. Chem. Soc., 2009, 131, 6318.
14 (a) X. Meng, Y. Huang, H. Zhao, P. Xie, J. Ma and R. Chen, Org. Lett.,
2009, 11, 991; (b) R. Ma, S. Xu, X. Tang, G. Wu and Z. He,
Tetrahedron, 2011, 67, 1053.
15 S. Xu, L. Zhou, R. Ma, H. Song and Z. He, Chem.–Eur. J., 2009,
15, 8698.
16 (a) E. Li, Y. Huang, L. Liang and P. Xie, Org. Lett., 2013, 15, 3138;
(b) M. Gicquel, C. Gomez, P. Retailleau, A. Voituriez and A. Marinetti,
Org. Lett., 2013, 15, 4002.
17 J. Zheng, Y. Huang and Z. Li, Org. Lett., 2013, 15, 5064.
18 H. Zhao, X. Meng and Y. Huang, Chem. Commun., 2013, 49, 10513.
19 CCDC 963723 (3a)†.
This work was supported financially by the National Natural
Science Foundation of China (21172115, 20972076) and the
Research Fund for the Doctoral Program of Higher Education
of China (20120031110002).
Notes and references
1 For some examples see: (a) Q. Khuong-Huu, A. Chiaroni, C. Riche,
H. Nguyen-Ngoc, K. Nguyen-Viet and F. J. Khuong-Huu, Chem. Nat.
Compd., 2000, 63, 1015; (b) S. V. Mudur, D. C. Swenson, J. B. Gloer,
J. Campbell and C. A. Shearer, Org. Lett., 2006, 8, 3191; (c) K.-I. Nihei,
Y. Asaka, Y. Mine, Y. Yamada, M. Iigo, T. Yanagisawa and I. J. Kubo,
Chem. Nat. Compd., 2006, 69, 975; (d) H. Zhang, O. A. Odeku, X.-N. Wang
and J.-M. Yue, Phytochemistry, 2008, 69, 271.
2 For selected reviews, see: (a) M. Lautens, W. Klute and W. Tam,
Chem. Rev., 1996, 96, 49; (b) J. H. Rigby, Acc. Chem. Res., 1993,
26, 579; (c) K. A. Jørgensen, Angew. Chem., Int. Ed., 2000, 39, 3558;
(d) E. J. Corey, Angew. Chem., Int. Ed., 2002, 41, 1650.
3 Phosphine-catalyzed intramolecular annulation to construct bi- or
polycyclic skeletons: (a) J.-C. Wang, S.-S. Ng and M. J. Krische, J. Am.
Chem. Soc., 2003, 125, 3682; (b) J.-C. Wang and M. J. Krische, Angew.
Chem., 2003, 115, 6035 (Angew. Chem., Int. Ed., 2003, 42, 5855);
(c) C. E. Henry and O. Kwon, Org. Lett., 2007, 9, 3069.
4 For reviews on phosphine-promoted cycloadditions (a) X. Lu, C. Zhang
and Z. Xu, Acc. Chem. Res., 2001, 34, 535; (b) D. H. Valentine and
J. H. Hillhouse, Synthesis, 2003, 317; (c) J. L. Methot and W. R. Roush,
Adv. Synth. Catal., 2004, 346, 1035; (d) X. Lu, Y. Du and C. Lu, Pure Appl.
Chem., 2005, 77, 1985; (e) C. K.-W. Kwong, M. Y. Fu, C. S.-L. Lam and
20 For mechanistic studies of the phosphine-catalyzed cycloaddition
reaction, see: (a) Y. Liang, S. Liu, Y. Xia, Y. Li and Z.-X. Yu,
Chem.–Eur. J., 2008, 14, 4361; (b) E. Mercier, B. Fonovic, C. Henry,
O. Kwon and T. Dudding, Tetrahedron Lett., 2007, 48, 3617; (c) Y. Xia,
Y. Liang, Y. Chen, M. Wang, L. Jiao, F. Huang, S. Liu, Y. Li and
Z.-X. Yu, J. Am. Chem. Soc., 2007, 129, 3470; (d) T. Dudding, O. Kwon
and E. Mercier, Org. Lett., 2006, 8, 3643; (e) X.-F. Zhu, C. E. Henry
and O. Kwon, J. Am. Chem. Soc., 2007, 129, 6722.
950 | Chem. Commun., 2014, 50, 948--950
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