Organic Letters
Letter
ASSOCIATED CONTENT
* Supporting Information
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Experimental procedures and characterization data for all new
compounds. This material is available free of charge via the
AUTHOR INFORMATION
Corresponding Author
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Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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This work was partly supported by the Ministry of Education,
Culture, Sports, Science and Technology, Japan (MEXT)
Platform for Drug Discovery, Informatics, and Structural Life
Science, and a Grant-in-Aid for Scientific Research on Innovative
Areas “Advanced Molecular Transformations by Organocatalysis.”
REFERENCES
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(1) (a) Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974.
(b) Hanson, R. M.; Sharpless, K. B. J. Org. Chem. 1986, 51, 1922.
(c) Zhang, W.; Basak, A.; Kosugi, Y.; Hoshino, Y.; Yamamoto, H. Angew.
Chem., Int. Ed. 2005, 44, 4389. (d) Egami, H.; Ogama, T.; Katsuki, T. J.
Am. Chem. Soc. 2010, 132, 5886. (e) Olivares-Romero, J. L.; Li, Z.;
Yamamoto, H. J. Am. Chem. Soc. 2013, 135, 3411. (f) Wang, C.;
Yamamoto, H. J. Am. Chem. Soc. 2014, 136, 1222.
(2) For synthetic applications of chiral epoxy alcohols, see: Riera, A.;
Moreno, M. Molecules 2010, 15, 1041.
(3) (a) Caron, M.; Sharpless, K. B. J. Org. Chem. 1985, 50, 1557.
(b) Chong, J. M.; Sharpless, K. B. J. Org. Chem. 1985, 50, 1560. (c) Behrens,
C. H.; Ko, S. Y.; Sharpless, K. B.; Walker, F. J. J. Org. Chem. 1985, 50, 5687.
(d) Behrens, B. H.; Sharpless, K. B. J. Org. Chem. 1985, 50, 5696.
(4) Chini, M.; Crotti, P.; Flippin, L. A.; Gardelli, C.; Giovani, E.;
Macchia, F.; Pineschi, M. J. Org. Chem. 1993, 58, 1221.
(5) For examples of the regioselective ring opening of 2,3-epoxy
alcohols with O-, S-, and halide nucleophiles, see: (a) Onaka, M.; Sugita,
K.; Takeuchi, H.; Izumi, Y. J. Chem. Soc., Chem. Commun. 1988, 117.
(b) Narender, M.; Reddy, M. S.; Nageswar, Y. V. D.; Rao, K. R. Helv.
Chim. Acta 2007, 90, 1107.
(6) For examples of the regioselective ring opening of 2,3-epoxy
alcohols with N-nucleophiles, see: (a) Maruoka, K.; Sano, H.;
Yamamoto, H. Chem. Lett. 1985, 14, 599. (b) Onaka, M.; Sugita, K.;
Izumi, Y. Chem. Lett. 1986, 15, 1327. (c) Caron, M.; Carlier, P. R.;
Sharpless, K. B. J. Org. Chem. 1988, 53, 5185. (d) Canas, M.; Poch, M.;
Verdaguer, X.; Moyano, A.; Pericas
1991, 32, 6931. (e) Benedetti, F.; Berti, F.; Norbedo, S. Tetrahedron Lett.
1998, 39, 7971. (f) Martín, R.; Islas, G.; Moyano, A.; Pericas, M. A.;
Riera, A. Tetrahedron 2001, 57, 6367. (g) Pasto, M.; Rodríguez, B.; Riera,
A.; Pericas, M. A. Tetrahedron Lett. 2003, 44, 8369. (h) Surendra, K.;
̀
, M. A.; Riera, A. Tetrahedron Lett.
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́
́
Krishnaveni, N. S.; Rao, K. R. Synlett 2004, 36, 506.
(7) Watanabe, T.; Imaizumi, T.; Chinen, T.; Nagumo, Y.; Shibuya, M.;
Usui, T.; Kanoh, N.; Iwabuchi, Y. Org. Lett. 2010, 12, 1040.
(8) Very recently, Yamamoto and Wang have reported an effective
catalytic system using a tungsten salt that has high regioselectivity.
Wang, C.; Yamamoto, H. J. Am. Chem. Soc. 2014, 136, 6888.
(9) For some “unexpected” results using reported methods, see:
(a) Alegret, C.; Santacana, F.; Riera, A. J. Org. Chem. 2007, 72, 7688.
(b) Tan, L.; Ma, D. Angew. Chem., Int. Ed. 2008, 46, 3614.
(10) (a) Meguro, M.; Asao, N.; Yamamoto, Y. Tetrahedron Lett. 1994,
35, 7395. (b) Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Chem.
Commun. 1995, 1021.
(11) Under Sharpless conditions, epoxide opening reaction did not
proceed using methyl ether 6b (see ref 3a).
(12) For details of the reaction conditions, see the Supporting
Information.
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dx.doi.org/10.1021/ol502264y | Org. Lett. XXXX, XXX, XXX−XXX