Organic Letters
Letter
(10) (a) Rueping, M.; Antonchick, A. P.; Brinkmann, C. Angew.
Chem., Int. Ed. 2007, 46, 6903. (b) Hamilton, G. L.; Kanai, T.; Toste,
F. D. J. Am. Chem. Soc. 2008, 130, 14984. (c) Zhang, Q.-W.; Fan, C.-
A.; Zhang, H.-J.; Tu, Y.-Q.; Zhao, Y.-M.; Gu, P.-M.; Chen, Z.-M.
Angew. Chem., Int. Ed. 2009, 48, 8572.
ASSOCIATED CONTENT
* Supporting Information
Complete experimental procedures and characterization data
for the prepared compounds and complete ref 16. This material
■
S
(11) (a) Lv, J.; Li, X.; Zhong, L.; Luo, S.-Z.; Cheng, J.-P. Org. Lett.
2010, 12, 1096. (b) Larson, S. E.; Li, G.-L.; Rowland, G. B.; Junge, D.;
Huang, R.; Woodcock, H. L.; Antilla, J. C. Org. Lett. 2011, 13, 2188.
(c) Ingle, G. K.; Liang, Y.-X.; Mormino, M. G.; Li, G.-L.; Fronczek, F.
R.; Antilla, J. C. Org. Lett. 2011, 13, 2054. (d) Li, G.-L.; Liang, T.-L.;
Wojtas, L.; Antilla, J. C. Angew. Chem., Int. Ed. 2013, 52, 4628.
(12) (a) Hatano, M.; Moriyama, K.; Maki, T.; Ishihara, K. Angew.
Chem., Int. Ed. 2010, 49, 3823. (b) Zhang, Z.-H.; Zheng, W.-H.;
Antilla, J. C. Angew. Chem., Int. Ed. 2011, 50, 1135. (c) Zheng, W.-H.;
Zhang, Z.-H.; Kaplan, M. J.; Antilla, J. C. J. Am. Chem. Soc. 2011, 133,
3339. (d) Drouet, F.; Lalli, C.; Liu, H.; Masson, G.; Zhu, J.-P. Org. Lett.
2011, 13, 94. (e) Rueping, M.; Nachtsheim, B. J.; Koenigs, R. M.;
Ieawsuwan, W. Chem.Eur. J. 2010, 16, 13116. (f) Rueping, M.;
Bootwicha, T.; Kambutong, S.; Sugiono, E. Chem.Asian J. 2012, 7,
1195. (g) Mao, Z.-J.; Li, W.-P.; Shi, Y.; Mao, H.-B.; Lin, A.-J.; Zhu, C.-
J.; Cheng, Y.-X. Chem.Eur. J. 2013, 19, 9754.
AUTHOR INFORMATION
Corresponding Authors
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Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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We are grateful for financial support from NSFC (21232007
and 21472180) and Ministry of Education.
(13) Tu, X.-F.; Gong, L.-Z. Angew. Chem., Int. Ed. 2012, 51, 11346.
(14) CCDC-941053 (4l) contains the supplementary crystallo-
graphic data for this paper. These data can be obtained free of charge
from the Cambridge Crystallographic Data Centre via www.ccdc.cam.
(15) Theoretical Inorganic Chemistry II; Albini, A.; Kisch, H., Eds.;
Springer: Berlin, 1976; pp 105−145.
(16) Frisch, M. J. et al. Gaussian 03, revision D.03; Gaussian, Inc.:
Wallingford, 2004. The full list of authors is in the Supporting
Information.
REFERENCES
■
(1) (a) The Diels−Alder Reaction: Selected Practical Methods;
Fringuelli, F., Taticchi, A., Eds.; John Wiley & Sons: New York,
2002. (b) Cycloaddition Reactions in Organic Synthesis; Kobayashi, S.,
Jørgensen, K. A., Eds.; Wiley-VCH: Weinheim, 2002; pp 151−209.
(c) Comprehensive Asymmetric Catalysis III; Jacobsen, E. N., Pfaltz, A.,
Yamamoto, H., Eds.; Springer: Berlin, 1999; pp 1237−1254.
(d) Gouverneur, V.; Reiter, M. Chem.Eur. J. 2005, 11, 5806.
(e) Jørgensen, K. A. Angew. Chem., Int. Ed. 2000, 39, 3558. (f) Tietze,
L. F.; Kettschau, G. Top. Curr. Chem. 1997, 189, 1. (g) Pellissier, H.
Tetrahedron 2009, 65, 2839. (h) Lin, L.-L.; Liu, X.-H.; Feng, X.-M.
Synlett 2007, 14, 2147. (i) Yamamoto, H.; Kawasaki, M. Bull. Chem.
Soc. Jpn. 2007, 80, 595.
(17) Hollis, T. K.; Bosnich, B. J. Am. Chem. Soc. 1995, 117, 4570.
(2) (a) Oscarsson, K.; Oscarson, S.; Vrang, L.; Hamelink, E.;
Hallberg, A.; Samuelsson, B. Bioorg. Med. Chem. 2003, 11, 1235.
(b) Zuccarello, G.; Bouzide, A.; Kvarnstrom, I.; Niklasson, G.;
Svensson, S. C. T.; Brisander, M.; Danielsson, H.; Nillroth, U.; Karlen,
A.; Hallberg, A.; Classon, B.; Samuelsson, B. J. Org. Chem. 1998, 63,
4898. (c) Cui, J.-Y.; Hao, J.-S.; Ulanovskaya, O. A.; Dundas, J.; Liang,
J.; Kozmin, S. A. Proc. Natl. Acad. Sci. U.S.A. 2011, 108, 6763.
(d) Oelke, A. J.; France, D. J.; Hofmann, T.; Wuitschik, G.; Ley, S. V.
Nat. Prod. Rep. 2011, 28, 1445. (e) Oelke, A. J.; France, D. J.;
Hofmann, T.; Wuitschik, G.; Ley, S. V. Angew. Chem., Int. Ed. 2010, 49,
6139. (f) Li, W.-H.; Gan, J.-G.; Ma, D.-W. Angew. Chem., Int. Ed. 2009,
48, 8891.
(3) Aburel, P. S.; Zhuang, W.; Hazell, R. G.; Jørgensen, K. A. Org.
Biomol. Chem. 2005, 3, 2344.
(4) Kawasaki, M.; Yamamoto, H. J. Am. Chem. Soc. 2006, 128, 16482.
(5) Liu, B.; Li, K.-N.; Luo, S.-W.; Huang, J.-Z.; Pang, H.; Gong, L.-Z.
J. Am. Chem. Soc. 2013, 135, 3323.
(6) For very early reports on chiral metal phosphate catalysis, see:
(a) Pirrung, M. C.; Zhang, J. Tetrahedron Lett. 1992, 33, 5987.
(b) McCarthy, N.; McKervey, M. A.; Tao, Y. Tetrahedron Lett. 1992,
33, 5983. (c) Inanaga, J.; Sujimoto, Y.; Inamoto, T. New J. Chem. 1995,
19, 707.
(7) For early reports on the use of chiral metal phosphates derived
from Akiyama−Terada catalysts in asymmetric catalysis, see:
(a) Mukherjee, S.; List, B. J. Am. Chem. Soc. 2007, 129, 11336.
(b) Hamilton, G. L.; Kang, E. J.; Mba, M.; Toste, F. D. Science 2007,
317, 496. For reviews, see: (c) Parra, A.; Reboredo, S.; Martín Castro,
́
A. M.; Aleman, J. Org. Biomol. Chem. 2012, 10, 5001. (d) Phipps, R. J.;
Hamilton, G. L.; Toste, F. D. Nat. Chem. 2012, 4, 603. (e) Mahlau, M.;
List, B. Angew. Chem., Int. Ed. 2013, 52, 518.
(8) (a) Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem.,
Int. Ed. 2004, 43, 1566. (b) Uraguchi, D.; Terada, M. J. Am. Chem. Soc.
2004, 126, 5356.
(9) For a review, see: Naodovic, M.; Yamamoto, H. Chem. Rev. 2008,
108, 3132.
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