Journal of the American Chemical Society
COMMUNICATION
acknowledges the Japan Society for the Promotion of Science for
Young Scientists for fellowship support.
’ REFERENCES
(1) (a) Faul, M. M.; Huff, B. E. Chem. Rev. 2000, 100, 2407.
(b) Kang, E. J.; Lee, E. Chem. Rev. 2005, 105, 4348.
(2) (a) Wolfe, J. P.; Hay, M. B. Tetrahedron 2007, 63, 261. (b) Jalce,
G.; Franck, X.; Figadꢀere, B. Tetrahedron: Asymmetry 2009, 20, 2537.
(3) (a) Catalytic Asymmetric Synthesis, 3rd ed.; Ojima, I., Ed.; John
Wiley & Sons: Hoboken, NJ, 2010. (b) Comprehensive Asymmetric
Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New
York, 1999; Vols. IÀIII. (c) Asymmetric Catalysis in Organic Synthesis;
Noyori, R., Ed.; John Wiley & Sons: New York, 1994.
(4) Catalytic intramolecular Michael reaction to generate THF:
Phillips, E. M.; Riedrich, M.; Scheidt, K. A. J. Am. Chem. Soc. 2010,
132, 13179.
(5) (a) Chen, G.; Ma, S. Angew. Chem., Int. Ed. 2010, 49, 8306.
(b) French, A. N.; Bissmire, S.; Wirth, T. Chem. Soc. Rev. 2004, 33, 354.
(c) Kang, S. H.; Kang, S. Y.; Park, C. M.; Kwon, H. Y.; Kim, M. Pure Appl.
Chem. 2005, 77, 1269. (d) Kang, S. H.; Lee, S. B.; Park, C. M. J. Am.
Chem. Soc. 2003, 125, 15748. (e) Kwon, H. Y.; Park, C. M.; Lee, S. B.;
Youn, J.-H.; Kang, S. H. Chem.—Eur. J. 2008, 14, 1023. (f) Kang, S. H.;
Park, C. M.; Lee, S. B.; Kim, M. Synlett 2004, 1279. (g) Hennecke, U.;
M€uller, C. H.; Fr€ohlich, R. Org. Lett. 2011, 13, 860. (h) Kang, S. H.; Kim,
M.; Kang, S. Y. Angew. Chem., Int. Ed. 2004, 43, 6177. (i) Kang, S. H.;
Kim, M. J. Am. Chem. Soc. 2003, 125, 4684. (j) Wilkinson, S. C.; Lozano,
O.; Schuler, M.; Pacheco, M. C.; Salmon, R.; Gouverneur, V. Angew.
Chem., Int. Ed. 2009, 48, 7083.
(6) For selected examples, see: (a) Huang, Y.; Unni, A. K.; Thadani,
A. N.; Rawal, V. H. Nature 2003, 424, 146. (b) Sigman, M. S.; Jacobsen,
E. N. J. Am. Chem. Soc. 1998, 120, 4901. (c) Uraguchi, D.; Terada, M.
J. Am. Chem. Soc. 2004, 126, 5356. (d) Akiyama, T.; Itoh, J.; Yokota, K.;
Fuchibe, K. Angew. Chem., Int. Ed. 2004, 43, 1566. (e) Hoffmann, S.;
Seayad, A. M.; List, B. Angew. Chem., Int. Ed. 2005, 44, 7424. (f) Storer,
R. I.; Carrera, D. E.; Ni, Y.; MacMillan, D. W. C. J. Am. Chem. Soc. 2006,
128, 84. (g) Nakashima, D.; Yamamoto, H. J. Am. Chem. Soc. 2006,
128, 9626. (h) Bauer, A.; Westk€amper, F.; Grimme, S.; Bach, T. Nature
2005, 436, 1139. (i) Kita, T.; Georgieva, A.; Hashimoto, Y.; Nakata, T.;
Nagasawa, K. Angew. Chem., Int. Ed. 2002, 41, 2832. (j) Hashimoto, T.;
Maruoka, K. J. Am. Chem. Soc. 2007, 129, 10054. (k) Uraguchi, D.;
Sakaki, S.; Ooi, T. J. Am. Chem. Soc. 2007, 129, 12392. (l) List, B.; Lerner,
R. A.; Barbas, C. F., III J. Am. Chem. Soc. 2000, 122, 2395. (m) Hayashi,
Y.; Itoh, T.; Aratake, S.; Ishikawa, H. Angew. Chem., Int. Ed. 2008,
47, 2082. (n) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S.
J. Am. Chem. Soc. 1999, 121, 10219. (o) Matsui, K.; Takizawa, S.; Sasai,
H. J. Am. Chem. Soc. 2005, 127, 3680. (p) Ishihara, K.; Nakano, K. J. Am.
Chem. Soc. 2007, 129, 8930. (q) Kawabata, T.; Muramatsu, W.; Nishio,
T.; Shibata, T.; Schedel, H. J. Am. Chem. Soc. 2007, 129, 12890. For
reviews, see: (r) Hydrogen Bonding in Organic Synthesis; Pihko, P. M.,
Ed.; Wiley-VCH: Weinheim, 2009. (s) Doyle, A. G.; Jacobsen, E. N.
Chem. Rev. 2007, 107, 5713. (t) Taylor, M. S.; Jacobsen, E. N. Angew.
Chem., Int. Ed. 2006, 45, 1520.
(7) (a) Okino, T.; Hoashi, Y.; Takemoto, Y. J. Am. Chem. Soc. 2003,
125, 12672. (b) Okino, T.; Hoashi, Y.; Furukawa, T.; Xu, X.; Takemoto,
Y. J. Am. Chem. Soc. 2005, 127, 119. (c) Vakulya, B.; Varga, S.; Csꢁampai,
A.; Soꢁos, T. Org. Lett. 2005, 7, 1967. (d) Hamza, A.; Schubert, G.; Soꢁos,
T.; Pꢁapai, I. J. Am. Chem. Soc. 2006, 128, 13151. (e) Connon, S. J. Chem.
ÀEur. J. 2006, 12, 5418.
(8) (a) Li, D. R.; Murugan, A.; Flack, J. R. J. Am. Chem. Soc. 2008,
130, 46. (b) Biddle, M. M.; Lin, M.; Scheidt, K. A. J. Am. Chem. Soc. 2007,
129, 3830.
(9) (a) Merz, H.; Stockhaus, K. J. Med. Chem. 1979, 22, 1475. (b)
Cerꢀe, V.; Mazzini, C.; Paolucci, C.; Pollicino, S.; Fava, A. J. Org. Chem.
1993, 58, 4567. (c) Paolucci, C.; Mazzini, C.; Fava, A. J. Org. Chem. 1995,
60, 169. (d) Laxmi, Y. R.; Santosh; Iyengar, D. S. Synthesis 1996, 594.
16713
dx.doi.org/10.1021/ja207322d |J. Am. Chem. Soc. 2011, 133, 16711–16713