Organic Letters
Letter
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possible without the decrease in the yield and enantioselectivity.
The utility of this protocol was successfully explored by the facile
preparation of medicinally interesting compounds in high yield
and enantiopurity.
ASSOCIATED CONTENT
* Supporting Information
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J. Am. Chem. Soc. 2007, 129, 3074. (i) Reis, O.; Eymur, S.; Reis, B.;
S
Demir, A. S. Chem. Commun. 2009, 1088. (j) Da, C. S.; Che, L. P.; Guo,
Q. P.; Wu, F. C.; Ma, X.; Jia, Y. N. J. Org. Chem. 2009, 74, 2541. (k) Wu,
F. C.; Da, C. S.; Du, Z. X.; Guo, Q. P.; Li, W. P.; Yi, L.; Jia, Y. N.; Ma, X. J.
Org. Chem. 2009, 74, 4812. (l) Pousse, G.; Le Cavelier, F.; Humphreys,
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(n) Henseler, A. H.; Ayats, C.; Pericas, M. A. Adv. Synth. Catal. 2014,
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The Supporting Information is available free of charge on the
Selection of optimal solvent and the loading of starting
materials, experimental procedures, characterization of
compounds, and HPLC and NMR spectra for compounds
(7) For organocatalytic asymmetric cross-aldol reactions of acetone
and trifluoroacetophenones, see: (a) Qiu, L. H.; Shen, Z. X.; Shi, C. Q.;
Liu, Y. H.; Zhang, Y. W. Chin. J. Chem. 2005, 23, 584. (b) Hara, N.;
Tamura, R.; Funahashi, Y.; Nakamura, S. Org. Lett. 2011, 13, 1662.
(c) Kokotos, C. G. J. Org. Chem. 2012, 77, 1131. (d) Duangdee, N.;
Harnying, W.; Rulli, G.; Neudoerfl, J.-M.; Groeger, H.; Berkessel, A. J.
Am. Chem. Soc. 2012, 134, 11196. (e) Yang, W.; Cui, Y.-M.; Zhou, W.;
Li, L.; Yang, K.-F.; Zheng, Z.-J.; Lu, Y.; Xu, L.-W. Synlett 2014, 25, 1461.
(f) Zong, H.; Huang, H.; Bian, G.; Song, L. J. Org. Chem. 2014, 79,
11768.
(8) In the process of this work, Ikemoto and co-workers released their
preliminary work on catalytic asymmetric cross-aldol reaction of
arylketones and trifluoroacetophenones Lutete, L. M.; Miyamoto, T.;
Ikemoto, T. Tetrahedron Lett. 2016, 57, 1220.
(9) Zheng, Y.; Xiong, H.-Y.; Nie, J.; Hua, M.-Q.; Ma, J.-A. Chem.
Commun. 2012, 48, 4308.
(10) (a) Guo, Q.; Bhanushali, M.; Zhao, C.-G. Angew. Chem., Int. Ed.
2010, 49, 9460. (b) Funabiki, K.; Itoh, Y.; Kubota, Y.; Matsui, M. J. Org.
Chem. 2011, 76, 3545. (c) Konda, S.; Guo, Q.-S.; Abe, M.; Huang, H.;
Arman, H.; Zhao, J. C.-G. J. Org. Chem. 2015, 80, 806.
(11) For reviews on catalytic asymmetric Mukaiyama aldol reactions,
see: (a) Machajewski, T. D.; Wong, C.-H. Angew. Chem., Int. Ed. 2000,
39, 1352. (b) Matsuo, J.-i.; Murakami, M. Angew. Chem., Int. Ed. 2013,
52, 9109. (c) Averill, D. J.; Allen, M. J. Catal. Sci. Technol. 2014, 4, 4129.
(12) For chiral zincate-catalyzed direct asymmetric aldol reactions of
arylketones, see: (a) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.;
Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871. (b) Trost, B.
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Y.-H.; Li, X.; Su, Y.-N. J. Org. Chem. 2008, 73, 7398.
X-ray data for the compound 5 (CIF)
AUTHOR INFORMATION
■
Corresponding Author
ORCID
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
We are grateful to the National Natural Science Foundation of
China for its financial support (No. 21072087).
■
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