Organic Letters
Letter
(2) (a) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem.
Rev. 1994, 94, 2483. (b) Song, C. E. In Cinchona Alkaloids in Synthesis
and Catalysis Ligands, Immobilization and Organocatalysis; Wiley-VCH:
Weinheim, 2009.
Scheme 5. Proposed Catalytic Cycle and Crude Reaction
ESI-MS Analysis
(3) (a) Hamza, A.; Schubert, G.; Soos, T.; Papai, I. J. Am. Chem. Soc.
2006, 128, 13151. (b) Blise, K.; Cvitkovic, M. W.; Gibbs, N. J.;
Roberts, S. F.; Whitaker, R. M.; Hofmeister, G. E.; Kohen, D. J. Org.
Chem. 2017, 82, 1347. (c) Grayson, M. N. J. Org. Chem. 2017, 82,
4396.
(4) Vakulya, B.; Varga, S.; Csampai, A.; Soos, T. Org. Lett. 2005, 7,
1967.
(5) Malerich, J. P.; Hagihara, K.; Rawal, V. H. J. Am. Chem. Soc. 2008,
130, 14416.
(6) (a) Oh, S. H.; Rho, H. S.; Lee, J. W.; Lee, J. E.; Youk, S. H.; Chin,
J.; Song, C. E. Angew. Chem., Int. Ed. 2008, 47, 7872. (b) Bae, H. Y.;
Sim, J. H.; Lee, J. W.; List, B.; Song, C. E. Angew. Chem., Int. Ed. 2013,
52, 12143.
(7) (a) Liu, Y.-L.; Zhou, F.; Cao, J.-J.; Ji, C.-B.; Ding, M.; Zhou, J.
Org. Biomol. Chem. 2010, 8, 3847. (b) Yan, W.; Wang, D.; Feng, J.; Li,
P.; Zhao, D.; Wang, R. Org. Lett. 2012, 14, 2512. (c) Hara, N.;
Nakamura, S.; Sano, M.; Tamura, R.; Funahashi, Y.; Shibata, N. Chem.
- Eur. J. 2012, 18, 9276. (d) Wang, D.; Liang, J.; Feng, J.; Wang, K.;
Sun, Q.; Zhao, L.; Li, D.; Yan, W.; Wang, R. Adv. Synth. Catal. 2013,
355, 548. (e) Liu, Y.-L.; Zhou, J. Chem. Commun. 2013, 49, 4421.
(f) Li, T.-Z.; Wang, X.-B.; Sha, F.; Wu, X.-Y. J. Org. Chem. 2014, 79,
4332. (g) Wang, X.-B.; Li, T.-Z.; Sha, F.; Wu, X.-Y. Eur. J. Org. Chem.
2014, 2014, 739. (h) Yu, J.-S.; Zhou, J. Org. Biomol. Chem. 2015, 13,
10968. (i) Bao, X.; Wang, B.; Cui, L.; Zhu, G.; He, Y.; Qu, J.; Song, Y.
Org. Lett. 2015, 17, 5168. (j) Montesinos-Magraner, M. M.; Vila, C.;
development and application of these trifunctional catalysts for
new efficient asymmetric transformations are currently in
progress in our laboratory.
ASSOCIATED CONTENT
* Supporting Information
Canton, R.; Blay, G.; Fernandez, I.; Munoz, M. C.; Pedro, J. R. Angew.
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Chem., Int. Ed. 2015, 54, 6320. (k) Arai, T.; Tsuchiya, K.; Matsumura,
E. Org. Lett. 2015, 17, 2416. (l) Nakamura, S.; Takahashi, S. Org. Lett.
2015, 17, 2590. (m) Liu, T.; Liu, W.; Li, X.; Peng, F.; Shao, Z. J. Org.
Chem. 2015, 80, 4950. (n) Montesinos-Magraner, M.; Vila, C.;
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The Supporting Information is available free of charge on the
Rendon-Patino, A.; Blay, G.; Fernandez, I.; Munoz, M. C.; Pedro, J. R.
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ACS Catal. 2016, 6, 2689. (o) He, Q.; Wu, L.; Kou, X.; Butt, N.; Yang,
G.; Zhang, W. Org. Lett. 2016, 18, 288. (p) Chen, J.; Wen, X.; Wang,
Y.; Du, F.; Cai, L.; Peng, Y. Org. Lett. 2016, 18, 4336.
All the experimental and spectroscopic data of
(8) (a) Okino, T.; Hoashi, Y.; Takemoto, Y. J. Am. Chem. Soc. 2003,
125, 12672. (b) Noble, A.; Anderson, J. C. Chem. Rev. 2013, 113,
AUTHOR INFORMATION
Corresponding Author
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2887. (c) Nunez, M. G.; Farley, A. J. M.; Dixon, D. J. J. Am. Chem. Soc.
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2013, 135, 16348. (d) Arai, T.; Matsumura, E.; Masu, H. Org. Lett.
Tel: (+91)-522-2668861.
ORCID
2014, 16, 2768. (e) Holmquist, M.; Blay, G.; Pedro, J. R. Chem.
Commun. 2014, 50, 9309. (f) Holmquist, M.; Blay, G.; Munoz, M. C.;
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Pedro, J. R. Adv. Synth. Catal. 2015, 357, 3857. (g) Kumar, A.; Kaur, J.;
Chimni, S. S.; Jassal, A. K. RSC Adv. 2014, 4, 24816. (h) Zhao, K.; Shu,
T.; Jia, J.; Raabe, G.; Enders, D. Chem. - Eur. J. 2015, 21, 3933.
(i) Fang, B.; Liu, X.; Zhao, J.; Tang, Y.; Lin, L.; Feng, X. J. Org. Chem.
2015, 80, 3332.
Notes
The authors declare no competing financial interest.
(9) Baricordi, N.; Benetti, S.; Biondini, G.; De Risi, C.; Pollini, G. P.
Tetrahedron Lett. 2004, 45, 1373.
ACKNOWLEDGMENTS
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(10) (a) Lv, H.; Tiwari, B.; Mo, J.; Xing, C.; Chi, Y. R. Org. Lett.
2012, 14, 5412. (b) Cui, B. D.; Zuo, J.; Zhao, J. Q.; Zhou, M. Q.; Wu,
Z. J.; Zhang, X. M.; Yuan, W. C. J. Org. Chem. 2014, 79, 5305.
(c) Chen, L.; Wu, Z. J.; Zhang, M. L.; Yue, D. F.; Zhang, X. M.; Xu, X.
Y.; Yuan, W. C. J. Org. Chem. 2015, 80, 12668. (d) Jiang, D.; Dong, S.;
Tang, W.; Lu, T.; Du, D. J. Org. Chem. 2015, 80, 11593. (e) Chen, K.
Q.; Li, Y.; Zhang, C. L.; Sun, D. Q.; Ye, S. Org. Biomol. Chem. 2016, 14,
2007. (f) Yang, P.; Wang, X.; Chen, F.; Zhang, Z. B.; Chen, C.; Peng,
L.; Wang, L. X. J. Org. Chem. 2017, 82, 3908.
(11) (a) Girgis, A. S. Eur. J. Med. Chem. 2009, 44, 91. (b) Murugan,
R.; Anbazhagan, S.; Narayanan, S. S. Eur. J. Med. Chem. 2009, 44, 3272.
(c) Gollner, A.; et al. J. Med. Chem. 2016, 59, 10147.
(12) Zhang, T.; Cheng, L.; Hameed, S.; Liu, L.; Wang, D.; Chen, Y. J.
Chem. Commun. 2011, 47, 6644.
This research was supported by SERB, New Delhi (SR/S1/
OC-97/2012 and EMR/2016/001161). B.J. thanks UGC, New
Delhi for research fellowship. We thank Director, CBMR for
research facilities.
DEDICATION
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Dedicated to Professor Chunni Lal Khetrapal (CBMR,
Lucknow) on his 80th birthday.
REFERENCES
■
(1) (a) Berkessel, A.; Groger, H. In Asymmetric Organocatalysis: From
Biomimetic Concepts to Applications in Asymmetric Synthesis; Wiley-
VCH: Weinheim, 2005. (b) List, B.; Yang, J. W. Science 2006, 313,
1584. (c) Mukherjee, S.; Yang, J. W.; Hoffmann, S.; List, B. Chem. Rev.
2007, 107, 5471. (d) MacMillan, D. W. C. Nature 2008, 455, 304.
(e) Lee, J. W.; Gall, T. M.; Opwis, K.; Song, C. E.; Gutmann, J. S.; List,
B. Science 2013, 341, 1225.
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