Organic Letters
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In conclusion, we have successfully developed an organo-
catalytic asymmetric Mannich reaction of allylic ketones and
cyclic ketimines by using a saccharide-derived chiral tertiary
amino-thiourea catalyst. This protocol provides a wide range of
tetrasubstituted α-amino esters with high regio-, diastereo-, and
enantioselectivities. Moreover, the products obtained can be
converted into optically active spiro- and tricyclic benzosultam
derivatives from simple modifications. Further development
and application of this Mannich reaction, as well as
investigation of the mechanism, is ongoing in our laboratory.
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ASSOCIATED CONTENT
Supporting Information
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*
S
(5) (a) Nakamura, S.; Sano, M.; Toda, A.; Nakane, D.; Masuda, H.
Chem. - Eur. J. 2015, 21, 3929. (b) Yin, X.; Zheng, Y.; Feng, X.; Jiang,
K.; Wei, X.; Gao, N.; Chen, Y. Angew. Chem., Int. Ed. 2014, 53, 6245.
(
6) (a) Zhu, B.; Zhang, W.; Lee, R.; Han, Z.; Yang, W.; Tan, D.;
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b) Tong, G.; Zhu, B.; Lee, R.; Yang, W.; Tan, D.; Yang, C.; Han, Z.;
Experimental details; spectral data of all the new
Crystallographic information on 3b (CIF)
(
Yan, L.; Huang, K.-W.; Jiang, Z. J. Org. Chem. 2013, 78, 5067. (c) Gu,
Y.; Wang, Y.; Yu, T.-Y.; Liang, Y.-M.; Xu, P.-F. Angew. Chem., Int. Ed.
2
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014, 53, 14128. (d) Zhan, G.; He, Q.; Yuan, X.; Chen, Y.-C. Org. Lett.
014, 16, 6000.
AUTHOR INFORMATION
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(7) (a) Liu, K.; Cui, H.-F.; Nie, J.; Dong, K.-Y.; Li, X.-J.; Ma, J.-A.
Org. Lett. 2007, 9, 923. (b) Li, X.-J.; Liu, K.; Ma, H.; Nie, J.; Ma, J.-A.
Synlett 2008, 2008, 3242. (c) Ma, H.; Liu, K.; Zhang, F.-G.; Zhu, C.-L.;
Nie, J.; Ma, J.-A. J. Org. Chem. 2010, 75, 1402. (d) Nie, J.; Li, X.-J.;
Zheng, D.-H.; Zhang, F.-G.; Cui, S.; Ma, J.-A. J. Fluorine Chem. 2011,
Notes
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32, 468. (e) Li, F.; Sun, L.; Teng, Y.; Yu, P.; Zhao, J. C.-G.; Ma, J.-A.
The authors declare no competing financial interest.
Chem. - Eur. J. 2012, 18, 14255. (f) Yuan, H.-N.; Wang, S.; Nie, J.;
Meng, W.; Yao, Q.; Ma, J.-A. Angew. Chem., Int. Ed. 2013, 52, 3869.
ACKNOWLEDGMENTS
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(g) Yuan, H.-N.; Li, S.; Nie, J.; Zheng, Y.; Ma, J.-A. Chem. - Eur. J.
This work was supported by the National Natural Science
Foundation of China, the National Basic Research Program of
China (973 Program, 2014CB745100), and the Tianjin
Municipal Science & Technology Commission
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013, 19, 15856. (h) Zhang, K.-F.; Li, F.; Nie, J.; Ma, J.-A. Sci. China:
Chem. 2014, 57, 265.
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