Please do not adjust margins
ChemComm
Page 4 of 5
COMMUNICATION
Journal Name
activation of SnCl4, the opening of the tetrahydropyran ring of
compound 3a will form intermediate E. Next, a semipinacol
rearrangement of intermediate E, i.e., the ring expansion of the
cyclobutanol moiety anti to the larger substituent at C3-position of
benzofuranium moiety, will produce intermediate F. Finally, a
reduction of the carbonyl group of F will lead to product 4a.
DOI: 10.1039/C9CC00811J
Wang and Y.-Q. Tu, Acc. Chem. Res., 2011, 44, 1207; (c) S.-H.
Wang, B.-S. Li, Y.-Q. Tu, Chem. Commun., 2014, 50, 2393.
15 Selected examples on enantioselective semipinacol
rearrangement: (a) B. M. Trost and J. Xie, J. Am. Chem. Soc.,
2006, 128, 6044; (b) T. Ooi, K. Ohmatsu and K. Maruoka, J.
Am. Chem. Soc., 2007, 129, 2410; (c) Q.-W. Zhang, C.-A. Fan,
H.-J. Zhang, Y.-Q. Tu, Y.-M. Zhao, P. Gu and Z.-M. Chen,
Angew. Chem. Int. Ed., 2009, 48, 8572; (d) E. Zhang, C.-A.
Fan, Y.-Q. Tu, F.-M. Zhang and Y.-L. Song, J. Am. Chem. Soc.,
2009, 131, 14626; (e) W. Li, J. Wang, X. Hu, K. Shen, W.
Wang, Y. Chu, L. Lin, X. Liu and X. Feng, J. Am. Chem. Soc.,
2010, 132, 8532; (f) Z.-M. Chen, Q.-W. Zhang, Z.-H. Chen, H.
Li, Y.-Q. Tu, F.-M. Zhang and J.-M. Tian, J. Am. Chem. Soc.,
2011, 133, 8818; (g) W. Li, X. Liu, X. Hao, Y. Cai, L. Lin and X.
Feng, Angew. Chem., Int. Ed., 2012, 51, 8644; (h) F.
Romanov-Michailidis, L. Guénée and A. Alexakis, Angew.
Chem. Int. Ed., 2013, 52, 9266; (i) W. Li, X. Liu, F. Tan, X. Hao,
J. Zheng, L. Lin and X. Feng, Angew. Chem., Int. Ed., 2013, 52,
10883; (j) B.-M. Yang, P.-J. Cai, Y.-Q. Tu, Z.-X. Yu, Z.-M. Chen,
S.-H. Wang, S.-H. Wang, F.-M Zhang, J. Am. Chem. Soc., 2015,
137, 8344; (k) H. Wu, Q. Wang, J. Zhu, Angew. Chem. Int. Ed.,
2016, 55, 15411; (l) S. Y. Shim, Y. Choi, D. H. Ryu, J. Am.
Chem. Soc., 2018, 140, 11184.
In conclusion, an enantioselective construction of multi-
substituted 3H-spiro[benzofuran-2,1'-cyclopentane] skeleton has
been realized through
a catalytic asymmetric one-pot [3+2]
cyclization/semipinacol rearrangement sequence. This method
provides an alternative and efficient strategy for the synthesis of
related bioactive molecules and their derivatives, and facilitates the
corresponding functional study. Currently, application of this
method in the synthesis of bioactive molecules is ongoing in the
same lab.
We thank Prof. Yong Tang of Shanghai Institute of Organic
Chemistry for his valuable suggestions and generosity in providing
the ligand L7. This work was supported by the National Natural
Science Foundation of China (21472077, 21502080 and 21772071,
21772076, 21871117), National Science and Technology Major
Project of the Ministry of Science and Technology of China
(2018ZX09711001-005-002), and the Fundamental Research Funds
for the Central Universities (lzujbky-2018-134).
16 Z.-W. Jiao, Y.-Q. Tu, Q. Zhang, W.-X. Liu, S.-Y. Zhang, S.-H.
Wang, F.-M. Zhang, S. Jiang, Nat. Comm., 2015, 6, 7332.
17 For selected reviews: (a) D. Magdziak, S. J. Meek and T. R. R.
Pettus, Chem. Rev., 2004, 104, 1383; (b) C.-X. Zhuo, W. Zhang
and S.-L. You, Angew. Chem. Int. Ed., 2012, 51, 12662; (c) B.
Hosamani, M. F. Ribeiro, E. N. da Silva Júnior and I. N. N.
Namboothiri, Org. Biomol. Chem., 2016, 14, 6913; (d) B. Yang
and S. Gao, Chem. Soc. Rev., 2018, 47, 7926; (e) W. Li, X. Xu,
P. Zhang and P. Li, Chem. Asian J., 2018, 13, 2350.
Conflicts of interest
There are no conflicts to declare.
Notes and references
18 Selected papers of 2-alkoxycarbonyl benzoquinones after
2000: (a) D. A. Evans, J. Wu, J. Am. Chem. Soc., 2003, 125,
10162; (b) G. A. Kraus and J. Kim, Tetrahedron Lett., 2004,
45, 1457; (c) C. Asche, W. Frank, A. Albertb. U. Kucklaenderc,
Bioorg. Med. Chem., 2005, 13, 819; (d) M. Helliwell, E. J.
Thomas, D. L. Whitehouse, Synthesis 2005, 19, 3235; (e) M.
A. Brimble, O. Laita and J. E. Robinson, Tetrahedron, 2006,
62, 3021 (f) T. B. Patrick, K. Gorrell and J. Rogers, J. Fluor.
Chem., 2007, 128, 710; (g) N. V. Sastry Mudiganti, S.
Claessens and N. De Kimpe, Tetrahedron, 2009, 65, 1716; (h)
L. Xia and Y. R. Lee, Org. Biomol. Chem., 2013, 11, 6097; (i) L.
Liao, C. Shu, M. Zhang, Y. Liao, X. Hu, Y. Zhang, Z. Wu, W.
Yuan and X. Zhang, Angew. Chem. Int. Ed., 2014, 53, 10471; (j)
M. Buccini and M. J. Piggott, Org. Lett., 2014, 16, 2490; (k) Y.-
H. Chen, D.-J. Cheng, J. Zhang, Y. Wang, X.-Y. Liu, B. Tan, J.
Am. Chem. Soc., 2015, 137, 15062; (l) Z. Chai, J.-N. Chen, Z.
Liu, X.-F. Li, P.-J. Yang, J.-P. Hu and G. Yang, Org. Biomol.
Chem., 2016, 14, 1024; (m) M. Moliterno, R. Cari, A. Puglisi,
A. Antenucci, C. Sperandio, E. Moretti, A. D. Sabato, R. Salvio,
and M. Bella, Angew. Chem. Int. Ed., 2017, 55, 6525; (n) H.
Zheng, C. Xu, Y. Wang, T. Kang, X. Liu, L. Lin, X. Feng, Chem.
Commun., 2017, 53, 6585; (o) C. Xu, H. Zheng, B. Hu, X. Liu, L.
Lin, X. Feng, Chem. Commun., 2017, 53, 9741; (p) Y.-H. Chen,
L.-W. Qi, F. Fang and B. Tan, Angew. Chem. Int. Ed., 2017, 56,
16308; (q) C. Qi, W. Wang, K. D. Reichl, J. McNeely and J. A.
Porco Jr., Angew. Chem. Int. Ed., 2018, 57, 2101; (r) Q.-J. Liu,
J. Zhu, X.-Y. Song, L. Wang, S. R. Wang, Y. Tang, Angew.
Chem. Int. Ed., 2018, 57, 3810.
1
2
3
(a) J. Sun, D. Shi, M. Ma, S. Li, S. Wang, S. Wang, L. Han, Y.
Yang, X. Fan, J. Shi, L. He, J. Nat. Prod., 2005, 68, 915; (b) P.
Chen, J. Wang, K. Liu, C. Li, J. Org. Chem., 2008, 73, 339.
K. Tamura, Y. Kato, A. Ishikawa, Y. Kato, M. Himori, M.
Yoshida, Y. Takashima, T. Suzuki, Y. Kawabe, O. Cynshi, T.
Kodama, E. Niki, M. Shimizu, J. Med. Chem., 2003, 46, 3083.
M. Van der Mey, A. Hatzelmann, G. P. M. Van Klink, I. J. Van
der Laan, G. J. Sterk, U. Thibaut, W. R. Ulrich, H. Timmerman,
J. Med. Chem., 2001, 44, 2523.
4
5
6
7
8
9
B. E. Roggo, F. Petersen, M. Sills, J. L. Roesel, T. Moerker, H.
H. Peter, J. Antibiot., 1996, 49, 13.
D. J.-Müller, M. Fleige, D. Schlüns, M. Wollenburg, C.G.
Daniliuc, J. Neugebauer, F. Glorius, ACS Catal., 2016, 6, 5735.
H.-P. Bi, X.-Y. Liu, F.-R. Gou, L.-N. Guo, X.-H. Duan, X.-Z. Shu,
Y.-M. Liang, Angew. Chem. Int. Ed., 2007, 46, 7068.
H. Ni, Z. Yu, W. Yao, Y. Lan, N. Ullah, Y. Lu, Chem. Sci., 2017,
8, 5699.
M. Wang, Z.-Q. Rong, Y. Zhao, Chem. Commun., 2014, 50,
15309.
Y. Wang, M. Jiang, J.-T. Liu, Chem. Eur. J., 2014, 20, 15315.
10 (a) M. Van der Mey, H. Boss, D. Couwenberg, A. Hatzelmann,
G. J. Sterk, K. Goubitz, H. Schenk, H. Timmerman, J. Med.
Chem., 2002, 45, 2526; (b) D. F. Shi, J. Song, J. Ma, A. Novack,
P. Pham, I. F. Nashashibi, C. J. Rabbat, C. Xin, U.S. Pat. Appl.
Publ., 20110313003, 22 Dec 2011.
11 (a) T. Dohi, Y. Hu, T. Kamitanaka, N. Washimi, Y. Kita, Org.
Lett., 2011, 13, 4814; (b) T. Dohi, Y. Hu, T. Kamitanaka, Y.
Kita, Tetrahedron, 2012, 68, 8424; (c) Y. Hu, T. Kamitanaka, Y.
Mishima, T. Dohi, Y. Kita, J. Org. Chem., 2013, 78, 5530.
12 (a) M. Braun, A. Hessamian-Alinejad, B. F. De Lacroix, B. H.
Alvarez, G. Fischer, Molecules, 2008, 13, 995; (b) X. Yao, X.
Xie, C. Wang, L. Zu, Org. Lett., 2015, 17, 4356.
19 For detailed analysis, please see ESI.
20 The CCDC Numbers of compounds 5a and 3d are 1883805
and 1883807.
13 J. W. Coe, K. E. Bianco, B. P. Boscoe, P. R. Brooks, E. C. Cox,
M. G. Vetelino, J. Org. Chem., 2003, 68, 9964.
4 | J. Name., 2012, 00, 1-3
This journal is © The Royal Society of Chemistry 20xx
Please do not adjust margins