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ChemComm
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COMMUNICATION
Journal Name
Y. Zi, X.-M. Lu, S.-Y. Wang and S.-J. Ji,DTOeIt:r1a0h.1e0d3r9o/Cn,5C2C001845,9760A,
232; (f) J. Dong, L. Pan, X. Xu and Q. Liu, Chem. Commun.,
2014, 50, 14797; (g) W. Tan, X. Li, Y.-X. Gong, M.-D. Ge and F.
Shi, Chem. Commun., 2014, 50, 15901; (h) C. Zhang, L.-X.
Zhang, Y. Qiu, B. Xu, Y. Zong and Q. X. Guo, RSC Adv., 2014, 4,
6916; (i) Y. Ma, J. You and F. Song, Chem. Eur. J., 2013, 19,
1189; (j) B. Prasad, B. Y. Sreenivas, G. R. Krishna, R.
Kapavarapu and M. Pal, Chem. Commun., 2013, 49, 6716; (k)
B. Xu, Z.-L. Guo, W.-Y. Jin, Z.-P. Wang, Y.-G. Peng and Q.-X.
Guo, Angew. Chem. Int. Ed., 2012, 51, 1059; (l) W. Zi, H. Wu
and F. D. Toste, J. Am. Chem. Soc., 2015, 137, 3225.
In conclusion, new Lewis acid–catalyzed cascade reactions
based on Nazarov cyclization of 1,4-pentadien-3-ols have been
developed, providing substituted cyclopenta[b]indoles and
spiro[indene-1,4´-quinoline]s in good yields. The advantages of
this approach are the use of inexpensive and environmentally
friendly FeBr3 as the catalyst, relatively mild reaction
conditions, and exclusive regio- and diastereoselectivities. This
facile and efficient methodology appears to be a useful tool for
the synthesis of biologically important cyclopenta[b]indole and
spiro[indene-1,4´-quinoline] derivatives.
11 (a) S. Dhiman and S. S. V. Ramasastry, Chem. Commun.,
2015, 51, 557; (b) G. Xia, X. Han and X. Lu, Org. Lett., 2014,
16, 2058; (c) K. Saito, H. Sogou, T. Suga, H. Kusama and N.
Iwasawa, J. Am. Chem. Soc., 2011, 133, 689; (d) K. S. Feldman,
D. K. Hester II, M. R. Iyer, P. Munson, C. S. López and O. N.
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Org. Lett., 2015, 17, 5116.
This study was supported by the NSF of China [grant
21372033 (to Z. W.)]; the Priority Academic Program
Development of Jiangsu Higher Education Institutions; Jiangsu
Key Laboratory of Advanced Catalytic Materials and
Technology (BM2012110); the Qing Lan Project (to Z. W.); the
NSF of the Jiangsu Higher Education Institutions of China
[grants 12KJA150002 (to Z. L.) and 14KJA150002 (to Z. W.)];
and the NSF [CHE 7096481 (to O. K.)]
12 For recent reviews on Nazarov cyclization, see: (a) D. R.
Wenz and J. R. de Alaniz, Eur. J. Org. Chem., 2015, 23; (b) M.
A. Tius, Chem. Soc. Rev., 2014, 43, 2979; (c) W. T. Spencer III,
T. Vaidya and A. J. Frontier, Eur. J. Org. Chem., 2013, 3621; (d)
N. Shimada, C. Stewart and M. A. Tius, Tetrahedron, 2011, 67,
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13 For a review on interrupted Nazarov cyclization, see: (a) T. N.
Grant, C. J. Rieder and F. G. West, Chem. Commun., 2009,
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cyclization, see: (b) Y. Kwon, D. J. Schatz and F. G. West,
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Liu, Angew. Chem. Int. Ed., 2014, 53, 10742; (e) M. J. Riveira
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4 | J. Name., 2012, 00, 1-3
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