Organic Letters
Letter
Imagawa, H.; Nishizawa, M. Org. Lett. 2008, 10, 1767. Our current
report disclosed the cyclization of vinyl ethers having electron-rich,
-neutral, and -withdrawing substituents.
(9) Kuninobu, Y.; Tatsuzaki, T.; Matsuki, T.; Takai, K. J. Org. Chem.
2011, 76, 7005.
ASSOCIATED CONTENT
* Supporting Information
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S
Experimental procedures, spectroscopic data for all new
1
compounds, and copies of H and 13C NMR spectra. This
(10) (a) Organobismuth Chemistry; Suzuki, H., Matano, Y., Eds.;
Elsevier: New York, 2001. (b) Briand, G. G.; Burford, N. Chem. Rev.
1999, 99, 2601. (c) Roux, C. L.; Dubac, J. Synlett 2002, 181.
(d) Leonard, N. M.; Wieland, L. C.; Mohan, R. S. Tetrahedron 2002,
58, 8373. (e) Gaspard-Iloughmane, H.; Le Roux, C. Eur. J. Org. Chem.
2004, 2517. (f) Gaspard-Iloughmane, H.; Le Roux, C. Trends Org.
Chem. 2006, 11, 65. (g) Hua, R. Curr. Org. Synth. 2008, 5, 1.
(h) Salvador, J. A. R.; Pinto, R. M. A.; Silvestre, S. M. Curr. Org. Synth.
2009, 6, 426. (i) Bothwell, J. M.; Krabbez, S. W.; Mohan, R. S. Chem.
Soc. Rev. 2011, 40, 4649. (j) Ollevier, T. Org. Biomol. Chem. 2013, 11,
2740. See also for our recent work: Murai, M.; Origuchi, K.; Takai, K.
94th CSJ. Annual Meeting 2014, 3B3−10.
(11) In the Bi(OTf)3-catalyzed reaction, the catalytic role of a
bismuth ion vs the activity of TfOH formed by hydrolysis from
residual water is still under debate. See: (a) Lambert, R. F.; Hinkle, R.
J.; Ammann, S. E.; Lian, Y.; Liu, J.; Lewis, S. E.; Pike, R. D. J. Org.
Chem. 2011, 76, 9269. (b) Godeau, J.; Olivero, S.; Antoniotti, S.;
material is available free of charge via the Internet at http://
AUTHOR INFORMATION
Corresponding Authors
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Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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This work was financially supported by a Grant-in-Aid (No.
26248030) from MEXT, Japan, and the Advanced Catalytic
Transformation program for Carbon utilization (ACT-C)
project of the Japan Science and Technology Agency (JST),
and MEXT program for promoting the enhancement of
research universities. The authors gratefully thank Mr. Ryo
Okada and Masahiro Nakamura (Okayama University) for
HRMS measurements.
́
Dunach, E. Org. Lett. 2011, 13, 3320. When 5 mol% TfOH was used
as a catalyst, 2a was obtained in 85% yield.
(12) Investigation of several transition-metal catalysts with 1a in
CH2ClCH2Cl (0.2 M) at 25 °C for 24 h: Sc(OTf)3, 76% (24 h);
[ReBr(CO)3(thf)]2 (2.5 mol%), 83% (24 h); Fe(OTf)2, 21% (24 h);
Cu(OTf)2, 88% (2 h); AgOTf, 26% (24 h); BiBr3, 59% (24 h). The
following catalysts did not afford 2a with the recovery of vinyl ether 1a
in >90% yield: Sm(OTf)3, Dy(OTf)3, Re2(CO)10, RhCl(PPh3)3,
Ir4(CO)12, BiI3.
(13) Investigation of solvents: toluene, 92%; hexane, 58%; CHCl3,
10%; Et2O, 65%; THF, 0%; MeCN, 92%; DMF, 0%; neat 17%.
(14) Li, B.; Devaraj, K.; Darcel, C.; Dixneuf, P. H. Tetrahedron 2012,
68, 5179.
(15) Treatment of 1a with 5 mol% of FeCl3 and 1 equiv of methanol
at 50 °C for 2 h gave 2a in 93% yield.
(16) The yield of 2d was decreased to 40% when the combination of
Bi(OTf)3 and MeOH was used as a promoter.
(17) (a) Kodomari, M.; Satoh, H.; Yoshitomi, S. J. Org. Chem. 1988,
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L. S.; Kaul, P. J. Org. Chem. 1994, 59, 7335. (c) Muathen, H. A.
Tetrahedron 1996, 52, 8863.
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dx.doi.org/10.1021/ol5018273 | Org. Lett. 2014, 16, 4134−4137