3
3. Wittig olefination: (a) Rein, T.; Pederson, T. M. Synthesis 2002, 579-
594; (b) Hoffmann, R. W. Angew. Chem. Int. Ed. 2001, 40, 1411-1416;
Lewis base catalytic moiety, but also as phase tag to facilitate
recycling and reuse of the catalyst. The explorations of chiral
tetraarylphosphonium salts in asymmetric catalysis are currently
underway in our laboratory.
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C.; Roller, S.; Hebel, A.; Haag, R.; Bannwarth, W. Angew. Chem. Int. Ed.
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references cited therein.
O
O
OEt
NO2
H3CO
H3CO
O
O
H3CO
H3CO
NO2
C6 (10 mol%)
+
OEt
rt, 1 h
OCH3
OCH3
2
1s
3s
Table 2. Recycling studies for the Micheal reaction of 1s and
ethyl acetoacetate.a
6. (a) Marcoux, D.; Charette, A. B. J. Org. Chem. 2008, 73, 590-593; (b)
Marcoux, D.; Charette, A. B. Adv. Synth. Catal. 2008, 350, 2967-2974.
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D.; Charette, A. B. Angew. Chem. Int. Ed. 2007, 46, 5011-5014.
8. (a) Zhang, L.; Luo, S. Z.; Cheng, J. P. Catal. Sci. Technol. 2011, 1, 507-
516. (b) Luo, S. Z.; Zhang, L.; Cheng, J. P. Chem. Asian. J. 2009, 4,
1184-1195.
9. (a) Hermeke, J.; Toy, P. H. Tetrahedron 2011, 67, 4103-4109. (b) Lin, Z.
H.; Chen, Z. X.; Yang, G. C.; Lu, C. F. Catal. Commun. 2013, 35, 1-5. (c)
Nie, X.; Lu, C. F.; Chen, Z. X.; Yang, G. C.; Nie, J. Q. J. Mol. Catal. A-
C. 2014, 393, 171-174. (d) Zimbron, J. M.; Dauphinais, M.; Charette, A.
B. Green Chem. 2015, 17, 3255-3259. (e) Poupon, J. C.; Boezio, A. A.;
Charette, A. B. Angew. Chem. Int. Ed. 2006, 45, 1415-1420. (f) Poupon,
J. C.; Marcoux, D.; Cloarec, J. M.; Charette, A. B. Org. Lett. 2007, 9,
3591-3594. (g) Ginisty, M.; Roy, M. N.; Charette, A. B. J. Org. Chem.
2008, 73, 590-593. (h) Werner, T.; Riahi, A. M.; Schramm, H. Synthesis,
2011, 21, 3482-3490. (i) Zhang, Q.; Zhang, S. B.; Li, S. H.
Number of Cycles
Yield (%)
1
2
3
4
5
6
97
94
91
85
84
77
a Reaction conditions: 1s (1.0 mmol), 2 (1.2 mmol), catalyst (0.10 mmol),
solvent (3.0 mL), room temperature, 1 h.
Acknowledgments
Macromolecules, 2012, 45, 2981-2988. (j) Tian, Y.; Xu, X.; Zhang, L.;
Qu, J. Org. Lett. 2016, 18, 268-271. (k) Toda, Y.; Komiyama, Y.;
Kikuchi, A.; Suga, H. ACS Catal. 2016, 6, 6906-6910.
This work was supported by NSFC (National Natural Science
Foundation of China, No. 21202009) and Beijing Normal
University.
10. Hellmut Hoffmann, Dieter Michael Chem. Ber. 1962, 523, 528-535.
11. For selected examples see: (a) Shi, X.; He, W.; Li, H.; Zhang, X.
Tetrahedron Lett. 2011, 52, 3204-3207. (b) Dong, Z.; Qiu, G.-F.; Zhou,
H.-B.; Dong, C. Tetrahedron: Asymmetry 2012, 23, 1550-1556. (c)
Hyoung, W.-M.; Dae, Y.-K. Tetrahedron Lett. 2012, 53, 6569-6572. (d)
Jia, C.-M.; Chen, D.; Zhang, C.-Y. Tetrahedron 2013, 69, 7320-7324. (e)
Liu, B.; Han, X.; Dong, Z. Tetrahedron: Asymmetry 2013, 24, 1276-1280.
12. (a) Tsogoeva, S. B. Eur. J. Org. Chem. 2007, 1701-1716. (b) Almasi, D.;
Alonso, D. A.; Najera, C. Tetrahedron: Asymmetry 2007, 18, 299-365. (c)
Vicario, J. L.; Badia, D.; Carrillo, L. Synthesis 2007, 2065-2092
13. Liu, X.; Qin, B.; Zhou, X.; He, B.; Feng, X. J. Am. Chem. Soc. 2005, 127,
12224-12225.
References and notes
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2. Shiyao Liu, Yusuke Kumatabara and Seiji Shirakawa