Organic Letters
Letter
(12) Baskaran and Chinthapally recently reported chemoselective
oxidation using stoichiometric amounts of TEMPO and NaOCl. See:
Chinthapally, K.; Baskaran, S. Org. Biomol. Chem. 2014, 12, 4305−4309.
(13) (a) Zhao, M.; Li, J.; Mano, E.; Song, Z.; Tschaen, D. M.;
Grabowski, E. J. J.; Reider, P. J. J. Org. Chem. 1999, 64, 2564−2566.
(b) Epp, J. B.; Widlanski, T. S. J. Org. Chem. 1999, 64, 293−295.
(14) (a) Shibuya, M.; Sato, T.; Tomizawa, M.; Iwabuchi, Y. Chem.
Commun. 2009, 1739−1741. (b) Shibuya, M.; Tomizawa, M.; Suzuki, I.;
Iwabuchi, Y. J. Am. Chem. Soc. 2006, 128, 8412−8413.
(15) (a) Lee, W.; Youn, J. H.; Kang, S. H. Chem. Commun. 2013, 49,
5231−5233. (b) Kuranaga, T.; Sesoko, Y.; Sakata, K.; Maeda, N.;
Hayata, A.; Inoue, M. J. Am. Chem. Soc. 2013, 135, 5467−5474.
(c) Uchida, K.; Ogawa, T.; Yasuda, Y.; Mimura, H.; Fujimoto, T.;
Fukuyama, T.; Wakimoto, T.; Asakawa, T.; Hamashima, Y.; Kan, T.
Angew. Chem., Int. Ed. 2012, 51, 12850−12853. (d) Watanabe, T.;
Imaizumi, T.; Chinen, T.; Nagumo, Y.; Shibuya, M.; Usui, T.; Kanoh, N.;
Iwabuchi, Y. Org. Lett. 2010, 12, 1040−1043.
(16) (a) Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102,
5974−5976. (b) Hanson, R. M.; Sharpless, K. B. J. Org. Chem. 1986, 51,
1922−1925.
(17) (a) Ganiev, I. M.; Timergazin, K. K.; Shereshovets, V. V.;
Grigor’ev, I. A.; Tolstikov, G. A. Russ. Chem. Bull. 2001, 50, 614−619.
(b) Ganiev, I. M.; Timerghazin, Q. K.; Khalizov, A. F.; Andriyashina, N.
M.; Shereshovets, V. V.; Volodarsky, L. B.; Tolstikov, G. A. Tetrahedron
Lett. 1999, 40, 4737−4740.
AUTHOR INFORMATION
■
Corresponding Author
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
We dedicate this work to the memory of Prof. Tsutomu Katsuki.
This work was partially supported by a Grant-in-Aid for Scientific
Research on Innovative Areas “Advanced Molecular Trans-
formations by Organocatalysts” and Platform for Drug
Discovery, Informatics, and Structural Life Science from
MEXT and by a Grant-in-Aid for Young Scientists (A) (No.
23689001) from JSPS.
REFERENCES
■
(1) (a) Ley, S. V.; Sheppard, T. D.; Myers, R. M.; Chorghade, M. S.
Bull. Chem. Soc. Jpn. 2007, 80, 1451−1472. (b) Groger, H. Adv. Synth.
Catal. 2001, 343, 547−558.
̈
(2) (a) McKeage, K. Clin. Drug. Invest. 2013, 33, 71−91. (b) Wilson, K.
E.; Burk, R. M.; Biftu, T.; Ball, R. G.; Hoogsteen, K. J. Org. Chem. 1992,
57, 7151−7158. (c) Murakami, Y.; Oshima, Y.; Yasumoto, T. Bull. Jpn.
Soc. Sci. Fish. 1982, 48, 69−72.
(3) (a) Bataille, C. J. R.; Donohoe, T. J. Chem. Soc. Rev. 2011, 40, 114−
128. (b) Kolb, H. C.; Vannieuwenhze, M. S.; Sharpless, K. B. Chem. Rev.
1994, 94, 2483−2547. (c) Schroder, M. Chem. Rev. 1980, 80, 187−213.
̈
(4) (a) Bonet, A.; Pubill-Ulldemolins, C.; Bo, C.; Gulyas, H.;
Fernandez, E. Angew. Chem., Int. Ed. 2011, 50, 7158−7161. (b) Pubill-
Ulldemolins, C.; Bonet, A.; Bo, C.; Gulyas, H.; Fernandez, E. Chem.
Eur. J. 2012, 18, 1121−1126.
(5) (a) Wang, Z.; Cui, Y. T.; Xu, Z. B.; Qu, J. J. Org. Chem. 2008, 73,
2270−2274. (b) Dey, S.; Powell, D. R.; Hu, C. H.; Berkowitz, D. B.
Angew. Chem., Int. Ed. 2007, 46, 7010−7014. (c) Schaus, S. E.; Brandes,
B. D.; Larrow, J. F.; Tokunaga, M.; Hansen, K. B.; Gould, A. E.; Furrow,
M. E.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 1307−1315.
(6) (a) Uesugi, S.; Watanabe, T.; Imaizumi, T.; Shibuya, M.; Kanoh,
N.; Iwabuchi, Y. Org. Lett. 2014, 16, 4408−4411. (b) Wang, C.;
Yamamoto, H. J. Am. Chem. Soc. 2014, 136, 6888−6891. (c) Caron, M.;
Sharpless, K. B. J. Org. Chem. 1985, 50, 1557−1560. (d) Suzuki, T.;
Saimoto, H.; Tomioka, H.; Oshima, K.; Nozaki, H. Tetrahedron Lett.
1982, 23, 3597−3600.
(7) (a) Schmidt, A.-K. C.; Stark, C. B. W. Org. Lett. 2011, 13, 5788−
5791. (b) Nicolaou, K. C.; Adsool, V. A.; Hale, C. R. H. Org. Lett. 2010,
12, 1552−1555. (c) Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991,
113, 7277−7287.
(8) (a) Shibuya, M.; Shibuta, T.; Fukuda, H.; Iwabuchi, Y. Org. Lett.
2012, 14, 5010−5013. (b) Shibuya, M.; Doi, R.; Shibuta, T.; Uesugi, S.;
Iwabuchi, Y. Org. Lett. 2012, 14, 5006−5009.
(9) (a) Ryabenkova, Y.; Miedziak, P. J.; Knight, D. W.; Taylor, S. H.;
Hutchings, G. J. Tetrahedron 2014, 70, 6055−6058. (b) Painter, R. M.;
Pearson, D. M.; Waymouth, R. M. Angew. Chem., Int. Ed. 2010, 49,
9456−9459.
(10) (a) Kubota, J.; Ido, T.; Kuroboshi, M.; Tanaka, H.; Uchida, T.;
Shimamura, K. Tetrahedron 2006, 62, 4769−4773. (b) Gancitano, P.;
Ciriminna, R.; Testa, M. L.; Fidalgo, A.; Ilharco, L. M.; Pagliaro, M. Org.
Biomol. Chem. 2005, 3, 2389−2392. (c) Testa, M. L.; Ciriminna, R.;
Hajji, C.; Garcia, E. Z.; Ciclosi, M.; Arques, J. S.; Pagliaro, M. Adv. Synth.
Catal. 2004, 346, 655−660. (d) Wong, C. H.; Matos, J. R. J. Org. Chem.
1985, 50, 1992−1994.
(11) (a) Liang, S.; Xu, Z.; Ye, T. Chem. Commun. 2010, 46, 153−155.
(b) Gruner, S. A. W.; Truffault, V.; Voll, G.; Locardi, E.; Stockle, M.;
Kessler, H. Chem.Eur. J. 2002, 8, 4366−4376. (c) Ikunaka, M.;
Matsumoto, J.; Nishimoto, Y. Tetrahedron: Asymmetry 2002, 13, 1201−
1208.
D
Org. Lett. XXXX, XXX, XXX−XXX