Recent Progress in the Chemistry of Keteniminium Salts
- Corresponding author: Zhang Lei, lzhang@zjnu.cn Peng Bo, pengbo@zjnu.cn
Citation:
Li Xiaojin, Sun Yan, Zhang Lei, Peng Bo. Recent Progress in the Chemistry of Keteniminium Salts[J]. Chinese Journal of Organic Chemistry,
;2016, 36(11): 2530-2544.
doi:
10.6023/cjoc201605046
Ye, J. T.; Ma, S. Acc. Chem. Res. 2014, 47, 989.
(b) Krause, N.; Winter, C. Chem. Rev. 2011, 111, 1994.
(c) Ma, S. Chem. Rev. 2005, 105, 2829.
(d) Allen, A. D.; Tidwell, T. D. Chem. Rev. 2013, 113, 7287.
(e) Lu, P.; Wang, Y. G. Chem. Soc. Rev. 2012, 41, 5687.
(f) Alajarin, M.; Marin-Luna, M.; Vidal, A. Eur. J. Org. Chem. 2012, 5637.
(g) Lu, P.; Wang, Y. G. Synlett 2010, 165.
Staudinger, H.; Meyer, J. Helv. Chim. Acta 1919, 619.
Xing, Y.; Cheng, B.; Wang, J.; Lu, P.; Wang, Y. G. Org. Lett. 2014, 16, 4814.
(b) Denmark, S. E.; Wilson, T. W. Angew. Chem., Int. Ed. 2012, 51, 9980.
Alajarín, M.; Vidal, A.; Ortín, M. M. Org. Biomol. Chem. 2003, 1, 4282.
doi: 10.1039/B310593H
Amold, B.; Regitz, M. Angew. Chem., Int. Ed. 1979, 18, 320.
(b) Alajarín, M.; Sánchez-Andrada, P.; Vidal, A.; Tovar, F. Eur. J. Org. Chem. 2004, 2636.
Molina, P.; Alajarín, M.; Vidal, A. J. Org. Chem. 1991, 56, 4008.
(b) Yang, Y. Y.; Shou, W. G.; Chen, Z. B.; Hong, D.; Wang, Y. G. J. Org. Chem. 2008, 73, 3928.
Alajarín, M.; Bonillo, B.; Ortín, M. M.; Sánchez-Andrada, P.; Vidal, A. Org. Lett. 2006, 8, 5645.
(b) Alajarín, M.; Bonillo, B.; Sánchez-Andrada, P.; Vidal, A. Bautista, D. Org. Lett. 2009, 11, 1365.
Snider, B. B. Chem. Rev. 1988, 88, 793.
doi: 10.1021/cr00087a005
Dekorver, K. A.; Li, H.-Y.; Lohse, A. G.; Hayashi, R.; Lu, Z.-J.; Zhang, Y.; Hsung, R. P. Chem. Rev. 2010, 110, 5064.
doi: 10.1021/cr100003s
Madelaine, C.; Valerio, V.; Maulide, N. Chem. Asian J. 2011, 6, 2224.
(b) Kaiser, D.; Maulide, N. J. Org. Chem. 2016, 81, 4421.
Marchand-Brynaert, J.; Ghosez, L. J. Am. Chem. Soc. 1972, 94, 2869.
doi: 10.1021/ja00763a061
Charette, A. B.; Grenon, M. Can. J. Chem. 2001, 79, 1694.
(b) Xiao, K.; Wang, A.; Huang, P. Q. Angew. Chem., Int. Ed. 2012, 51, 8314.
(c) Bechara, W. S.; Pelletier, G.; Charette, A. B. Nat. Chem. 2012, 4, 228.
Zificsak, C. A.; Mulder, J. A.; Hsung, R. P.; Rameshkumar, C.; Wei, L.-L. Tetrahedron 2001, 57, 7575.
doi: 10.1016/S0040-4020(01)00681-0
Rens, M.; Ghosez, L. Tetrahedron Lett. 1970, 11, 3765.
doi: 10.1016/S0040-4039(01)98583-1
Yashi, H.; Yorimitsu, H.; Oshima, K. Chem. Lett. 2008, 37, 40.
doi: 10.1246/cl.2008.40
Xu, S.-J.; Liu, J.-Q.; Hu, D.-H.; Bi, X.-H. Green. Chem. 2015, 17, 184.
doi: 10.1039/C4GC01328J
Compain, G.; Jouvin, K.; Martin-Mingot, A.; Evano, G.; Marrot, J.; Thibaudeau, S. Chem. Commun. 2012, 48, 5196.
doi: 10.1039/c2cc31768k
Métayer, B.; Compain, G.; Jouvin, K.; Martin-Mingot, A.; Bachmann, C.; Marrot, J.; Evano, G.; Thibaudeau, S. J. Org. Chem. 2015, 80, 3397.
doi: 10.1021/jo502699y
Tona, V.; de la Torre, A.; Padmanaban, M.; Ruider, S.; González, L.; Maulide, N. J. Am. Chem. Soc. 2016, 138, 8348.
doi: 10.1021/jacs.6b04061
Tona, V.; Ruider, S. A.; Berger, M.; Shaaban, S.; Padmanaban, M.; Xie, L.-G.; González, L.; Maulide, N. Chem. Sci. 2016, 7, 6032.
doi: 10.1039/C6SC01945E
Theunissen, C.; Métayer, B.; Henry, N.; Compain, G.; Marrot, J.; Martin-Mingot, A.; Thibaudeau, S.; Evano, G. J. Am. Chem. Soc. 2014, 136, 12528.
doi: 10.1021/ja504818p
Lecomte, M.; Evano, G. Angew. Chem., Int. Ed. 2016, 55, 4547.
doi: 10.1002/anie.201510729
Ghosez, L. Angew. Chem., Int. Ed. 1972, 11, 852.
Zhang, Y.-S. Tetrahedron Lett. 2005, 46, 6483.
(b) Zhang, Y.-S. Tetrahedron 2006, 62, 3917.
Ghosez, L.; Notte, P.; Bernard-Henriet, C.; Maurin, R. Heterocyles 1981, 15, 1179.
doi: 10.3987/S-1981-02-1179
Zhang, Y.-S.; Hsung, R. P.; Zhang, X.-J.; Huang, J.; Slafer, B. W.; Davis, A. Org. Lett. 2005, 7, 1047.
doi: 10.1021/ol0473391
Lumbroso, A.; Behra, J.; Kolleth, A.; Dakas, P. Y.; Karadeniz, U.; Catak, S.; Sulzer-Mossé, S.; De Mesmaker, A. Tetrahedron Lett. 2015, 56, 6541.
doi: 10.1016/j.tetlet.2015.09.103
Villedieu-Percheron, J.; Catak, S.; Zurwerra, D.; Staiger, R.; Lachia, M.; De Mesmaker, A. Tetrahedron Lett. 2014, 55, 2446.
doi: 10.1016/j.tetlet.2014.02.135
Yamaoka, Y.; Yoshida, T.; Shinozaki, M.; Yamada, K.-I.; Takasu, K. J. Org. Chem. 2015, 80, 957.
doi: 10.1021/jo502467m
Viehe, H. G.; Buijle, R.; Fuks, R.; Merényi, R.; Oth, J. M. F. Angew. Chem., Int. Ed. 1967, 6, 77.
(b) Viehe, H. G. Angew. Chem., Int. Ed. 1967, 6, 767.
Ghosez, L.; Haveaux, B.; Viehe, H. G. Angew. Chem., Int. Ed. 1969, 8, 454.
doi: 10.1002/(ISSN)1521-3773
Marchand-Brynaert, J.; Ghosez, L. J. Am. Chem. Soc. 1972, 94, 2870.
doi: 10.1021/ja00763a062
Falmagne, J.-B.; Escudero, J.; Taleb-Sahraoui, S.; Ghosez, L. Angew. Chem., Int. Ed. 1981, 20, 879.
doi: 10.1002/(ISSN)1521-3773
Houge, C.; Frisque-Hesbain, A. M.; Mockel, A.; Ghosez, L. J. Am. Chem. Soc. 1982, 104, 2920.
doi: 10.1021/ja00374a036
Brown, R. C. D.; Bataille, C. J. R.; Bruton, G.; Hinks, J. D.; Swain, N. A. J. Org. Chem. 2001, 66, 6719.
doi: 10.1021/jo015829q
Shim, P.-J.; Kim, H.-D. Tetrahedron Lett. 1998, 39, 9517.
doi: 10.1016/S0040-4039(98)02228-X
Depré, D.; Chen, L.-Y.; Ghosez, L. Tetrahedron 2003, 59, 6797.
doi: 10.1016/S0040-4020(03)00920-7
O'Brien, J. M.; Kingsbury, J. S. J. Org. Chem. 2011, 76, 1662.
doi: 10.1021/jo102257k
Kolleth, A.; Lumbroso, A.; Tanriver, G.; Catak, S.; Sulzer-Mossé, S.; De Mesmaker, A. Tetrahedron Lett. 2016, 57, 2697.
doi: 10.1016/j.tetlet.2016.04.092
Lumbroso, A.; Catak, S.; Sulzer-Mossé, S.; De Mesmaker, A. Tetrahedron Lett. 2014, 55, 5147.
(b) Lumbroso, A.; Catak, S.; Sulzer-Mossé, S.; De Mesmaker, A. Tetrahedron Lett. 2014, 55, 6721.
Domigo, L. R.; Ríos-Gutiérrez, M.; Pérez, P. Tetrahedron 2015, 71, 2421.
doi: 10.1016/j.tet.2015.02.070
Shindoh, N.; Kitaura, K.; Takemoto, Y.; Takasu, K. J. Am. Chem. Soc. 2011, 133, 8470.
doi: 10.1021/ja202576e
Ficini, J. Tetrahedron Lett. 1966, 7, 6425.
doi: 10.1016/S0040-4039(00)76120-X
Mulder, J. A.; Hsung, R. P.; Frederick, M. O.; Tracey, M. R.; Zificsak, C. A. Org. Lett. 2002, 4, 1383.
doi: 10.1021/ol020037j
Madelaine, C.; Valerio, V.; Maulide, N. Angew. Chem., Int. Ed. 2010, 49, 1583.
doi: 10.1002/anie.200906416
Valerio, V.; Madelaine, C.; Maulide, N. Chem. Eur. J. 2011, 17, 4742.
doi: 10.1002/chem.201003591
Peng, B.; O'Donovan, D. H.; Jurberg, I. D.; Maulide, N. Chem. Eur. J. 2012, 18, 16292.
doi: 10.1002/chem.201203293
Peng, B.; Geerdink, D.; Maulide, N. J. Am. Chem. Soc. 2013, 135, 14968.
doi: 10.1021/ja408856p
Peng, B.; Geerdink, D.; Farès, C.; Maulide, N. Angew. Chem., Int. Ed. 2014, 53, 5462.
doi: 10.1002/anie.v53.21
Peng, B.; Huang, X.-L.; Xie, L.-G.; Maulide, N. Angew. Chem., Int. Ed. 2014, 53, 8718
doi: 10.1002/anie.201310865
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