Organic Letters
Letter
V.; Vovk, M. V. Tetrahedron: Asymmetry 2008, 19, 761. (c) Hara, N.;
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(5) Our modified method to synthesize hemiaminals was based on
the previously reported literature; see: (a) Takahashi, M.; Ohtsuki, K.;
Taga, T.; Chohnan, Y. Heterocycles 1998, 48, 1643. (b) Singh, S. K.;
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including alkyl and aryl ketones, were used to provide various
β-amino ketones with high control of the stereoselectivity.
Moreover, two important intermediates, ai and bi, were
detected and identified in the reaction. The detailed mechanism
study revealed the first intermolecular Mannich reaction of
alkyl-substituted N-sulfonyl ketimines with acetone. In addition,
this useful method offers a general access to fluoroalkyl β-amino
alcohols.
ASSOCIATED CONTENT
* Supporting Information
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S
(6) Dewick, P. M. Medicinal Natural Products: A Biosynthetic
Approach; Wiley-VCH: Chicheter, U.K., 2009.
The Supporting Information is available free of charge on the
(7) For the reaction of hemiaminals, see: (a) Pilli, R. A.; Dias, L. C.;
Maldaner, A. O. J. Org. Chem. 1995, 60, 717. (b) Aggarwal, V. K.;
Astle, C. J.; Rogers-Evans, M. Org. Lett. 2004, 6, 1469. (c) Raheem, I.
T.; Thiara, P. S.; Peterson, E. A.; Jacobsen, E. N. J. Am. Chem. Soc.
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A. J. Org. Chem. 2009, 74, 590. (e) Kamogawa, S.; Ikeda, T.; Kuriyama,
M.; Matsumura, Y.; Onomura, O. Heterocycles 2010, 82, 325.
(f) Knowles, R. R.; Lin, S.; Jacobsen, E. N. J. Am. Chem. Soc. 2010,
132, 5030. (g) Shi, S.; Wei, X.; Shimizu, Y.; Kanai, M. J. Am. Chem. Soc.
2012, 134, 17019. (h) Koley, D.; Srinivas, K.; Krishna, Y.; Gupta, A.
RSC Adv. 2014, 4, 3934. (i) Koley, D.; Krishna, Y.; Srinivas, K.; Khan,
A. A.; Kant, R. Angew. Chem., Int. Ed. 2014, 53, 13196.
Typical experimental procedure and characterization for
AUTHOR INFORMATION
Corresponding Author
■
Notes
The authors declare no competing financial interest.
(8) For reviews, see: (a) Notz, W.; Tanaka, F.; Barbas, C. F., III Acc.
Chem. Res. 2004, 37, 580. (b) Verkade, J. M. M.; Hemert, L. J. C.;
Quaedflieg, P. J. L. M.; Rutjes, F. P. J. T. Chem. Soc. Rev. 2008, 37, 29.
Recently examples: (c) Ren, Y.; Wang, Y.; Liu, S.; Pan, K.
ChemCatChem 2014, 6, 2985. (d) Mondal, B.; Pan, S. C. Org. Biomol.
Chem. 2014, 12, 9789. (e) Zhang, S.; Li, L.; Hu, Y.; Zha, Z.; Wang, Z.;
Loh, T. Org. Lett. 2015, 17, 1050.
ACKNOWLEDGMENTS
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The authors are grateful to the National Nature Science
Foundation of China (2127222, 91213303, 21432009,
21472177).
(9) (a) For details of the 19F NMR study, see pp S10−S13 of the
(10) For details of the HRMS study see pp S15−S17 of the
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