Journal of the American Chemical Society
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handle to deliver a variety of enantiomerically enriched molecules.
Further research to use quinone imine ketals in other asymmetric
transformations is currently underway in this laboratory.
(8) Jensen, K. L.; Franke, P. T.; Nielsen, L. T.; Daasbjerg, K.; Jørgensen,
K. A. Angew., Chem. Int. Ed. 2010, 49, 129.
(9) (a) Hashimoto, T.; Maruoka, K. J. Am. Chem. Soc. 2007, 129, 10054.
(b) Hashimoto, T.; Uchiyama, N.; Maruoka, K. J. Am. Chem. Soc. 2008,
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(10) For general reviews on chiral Brønsted acid catalysis, see: (a) Aki-
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1929.
Supporting Information
Experimental details and characterization data. This material is
AUTHOR INFORMATION
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Corresponding Author
(11) For a review, see: Matsubara, R.; Kobayashi, S. Acc. Chem. Res.
2008, 41, 292.
(12) For selected examples on the use of enecarbamates and enamides as
nucleophile in chiral Brønsted acid catalysis, see: (a) Terada, M.; Machi-
oka, K.; Sorimachi, K. Angew., Chem. Int. Ed. 2006, 45, 2254. (b) Terada,
M.; Machioka, K.; Sorimachi, K. J. Am. Chem. Soc. 2007, 129, 10336. (c)
Terada, M.; Soga, N.; Momiyama, N. Angew. Chem., Int. Ed. 2008, 47,
4122. (d) Terada, M.; Machioka, K.; Sorimachi, K. Angew. Chem., Int. Ed.
2009, 48, 2553. (e) Liu, H.; Dagousset, G.; Masson, G.; Retailleau, P.;
Zhu, J. J. Am. Chem. Soc. 2009, 131, 4598. (f) Dagousset, G.; Drouet, F.;
Masson, G.; Zhu, J. Org. Lett. 2009, 11, 5546. (g) Dagousset, G.; Zhu, J.;
Masson, G. J. Am. Chem. Soc. 2011, 133, 14804. (h) Alix, A.; Claudia, L.;
Retailleau, P.; Masson, G. J. Am. Chem. Soc. 2012, 134, 10389. (i) Lu,
M.; Lu, Y.; Zhu, D.; Zeng, X.; Li, X.; Zhong, G. Angew. Chem., Int. Ed.
2010, 49, 8588.
(13) For the chiral Brønsted acid catalyzed enantioselective synthesis of
hemiaminal ethers, see: (a) Li, G.; Fronczek, F. R.; Antilla, J. C. J. Am.
Chem. Soc. 2008, 130, 12216. (b) Vellalath, S.; Čorić, I.; List, B. Angew.
Chem., Int. Ed. 2010, 49, 9749.
(14) Honjo, T.; Phipps, R. J.; Rauniyar, V.; Toste, F. D. Angew. Chem.,
Int. Ed. 2012, 51, 9684.
ACKNOWLEDGMENT
This work was partially supported by a Grant-in-Aid for Scientific
Research from the MEXT (Japan). H.N. thank a Grant-in-Aid for
the Research Fellowship of JSPS for Young Scientists.
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