4
Tetrahedron
Catal. 2017, 359, 4165-4169; (o) Ding, R.; Wolf, C., Org. Lett.
2018, 20, 892-895.
spiro[pyrrolidin-3,2’-oxindoles] containing halogenated CQCS
and CF3 units, each of which are highly important structural
motifs in medicinal chemistry research. The halogen-containing
products can be stereoselectively transformed into sulfurated
derivatives by nucleophilic substitution (SN2) reactions,
indicating that they may serve as interesting compounds in the
exploitation of covalent inhibitors with potential biological
activity. Further studies on the bioactivity of the resulting
compounds are underway in our laboratories.
4.
(a) Marti, C.; Carreira, Erick M., Eur. J. Org. Chem. 2003, 2003,
2209-2219; (b) Galliford, C. V.; Scheidt, K. A., Angew. Chem. Int.
Ed. Engl. 2007, 46, 8748-8758; (c) Zhou, F.; Liu, Y.-L.; Zhou, J.,
Adv. Synth. Catal. 2010, 352, 1381-1407; (d) Shi, F.; Tao, Z. L.;
Luo, S. W.; Tu, S. J.; Gong, L. Z., Chem-Eur. J. 2012, 18, 6885-
6894; (e) Singh, G. S.; Desta, Z. Y., Chem. Rev. 2012, 11, 6104-
6155; (f) Rios, R., Chem. Soc. Rev. 2012, 41, 1060-1074; (g) Liu,
Y.; Wang, H.; Wan, J., Asian J. Org. Chem. 2013, 2, 374-386; (h)
Hong, L.; Wang, R., Adv. Synth. Catal. 2013, 355, 1023-1052.
Tian, L.; Hu, X. Q.; Li, Y. H.; Xu, P. F., Chem. Commun. 2013,
49, 7213-7215.
(a) Sun, Q.; Li, X.; Su, J.; Zhao, L.; Ma, M.; Zhu, Y.; Zhao, Y.;
Zhu, R.; Yan, W.; Wang, K.; Wang, R., Adv. Synth. Catal. 2015,
357, 3187-3196; (b) Ma, M.; Zhu, Y.; Sun, Q.; Li, X.; Su, J.;
Zhao, L.; Zhao, Y.; Qiu, S.; Yan, W.; Wang, K.; Wang, R., Chem.
Commun. 2015, 51, 8789-8792.
5.
6.
Conflicts of interest
There are no conflicts to declare.
Acknowledgements
We are grateful for financial support from the National Natural
Science Foundation of China (81573588, 81773889, 81630101
and 81891012), the Science & Technology Department of
Sichuan Province (2017JZYD0001 and 2017JY0323).
7.
(a) Wang, Z. H.; Wu, Z. J.; Yue, D. F.; Hu, W. F.; Zhang, X. M.;
Xu, X. Y.; Yuan, W. C., Chem. Commun. 2016, 52, 11708-11711;
(b) Huang, W.-J.; Chen, Q.; Lin, N.; Long, X.-W.; Pan, W.-G.;
Xiong, Y.-S.; Weng, J.; Lu, G., Org. Chem. Front. 2017, 4, 472-
482; (c) Zhi, Y.; Zhao, K.; von Essen, C.; Rissanen, K.; Enders,
D., Synlett 2017, 28 (20), 2876-2880; (d) Song, Y. X.; Du, D. M.,
J. Org. Chem. 2018, 83, 9278-9290; (e) You, Y.; Lu, W. Y.;
Wang, Z. H.; Chen, Y. Z.; Xu, X. Y.; Zhang, X. M.; Yuan, W. C.,
Org. Lett. 2018, 20, 4453-4457; (f) Zhao, X.; Xiong, J.; An, J.;
Yu, J.; Zhu, L.; Feng, X.; Jiang, X., Org. Chem. Front. 2019, 6,
1989-1995; (g) Li, B.; Gao, F.; Feng, X.; Sun, M.; Guo, Y.; Wen,
D.; Deng, Y.; Huang, J.; Wang, K.; Yan, W., Org. Chem. Front.
2019, 6, 1567-1571; (h) Lin, Y.; Song, Y.-X.; Du, D.-M., Adv.
Synth. Catal. 2019, 361, 1064-1070; (i) Zhu, W.-R.; Zhang, Z.-
W.; Huang, W.-H.; Lin, N.; Chen, Q.; Chen, K.-B.; Wang, B.-C.;
Weng, J.; Lu, G., Synthesis 2019, 51, 1969-1979; (j) Zhao, B. L.;
Du, D. M., Adv. Synth. Catal. 2019, 361, 3412-3419; (k) Wu, X.-
Y.; Gao, Y.-N.; Shi, M., Eur. J. Org. Chem. 2019, 2019, 1620-
1626; (l) Wang, C.; Wen, D.; Chen, H.; Deng, Y.; Liu, X.; Liu, X.;
Wang, L.; Gao, F.; Guo, Y.; Sun, M.; Wang, K.; Yan, W., Org.
Biomol. Chem. 2019, 17, 5514-5519; (m) Gao, X. Y.; Yan, R. J.;
Xiao, B. X.; Du, W.; Albrecht, L.; Chen, Y. C., Org. Lett. 2019,
21, 9628-9632; (n) Yang, X.-C.; Liu, J.-Y.; Liu, Z.; Hu, X.-Q.;
Xu, P.-F., J. Org. Chem. 2019, 84, 13871-13880.
(a) Yang, M. C.; Peng, C.; Huang, H.; Yang, L.; He, X. H.;
Huang, W.; Cui, H. L.; He, G.; Han, B., Org. Lett. 2017, 19, 6752-
6755;
(b) Zhao, Q.; Peng, C.; Huang, H.; Liu, S. J.; Zhong, Y. J.; Huang,
W.; He, G.; Han, B., Chem. Commun. 2018, 54, 8359-8362;
(c) Wang, B.; Wang, X. H.; Huang, W.; Zhou, J.; Zhu, H. P.;
Peng, C.; Han, B., J. Org. Chem. 2019, 84, 10349-10361;
(d) Zhou, J.; Wang, B.; He, X. H.; Liu, L.; Wu, J.; Lu, J.; Peng, C.;
Rao, C. L.; Han, B., J. Org. Chem. 2019, 84, 5450-5459.
(a) Muruganantham, R.; Mobin, S. M.; Namboothiri, I. N., Org.
Lett. 2007, 9, 1125-1128; (b) Rueping, M.; Parra, A., Org. Lett.
2010, 22, 5281-5283; (c) Fan, L. P.; Li, P.; Li, X. S.; Xu, D. C.;
Ge, M. M.; Zhu, W. D.; Xie, J. W., J. Org. Chem. 2010, 75, 8716-
8719; (d) Ayyagari, N.; Jose, D.; Mobin, S. M.; Namboothiri, I.
N. N., Tetrahedron Letters 2011, 52, 258-262; (e) Xie, J.-W.; Li,
P.; Wang, T.; Zhou, F.-T., Tetrahedron Letters 2011, 52, 2379-
2382; (f) Martín-Santos, C.; Jarava-Barrera, C.; Parra, A.; Esteban,
F.; Navarro-Ranninger, C.; Alemán, J., ChemCatChem 2012, 4,
976-979; (g) Jarava-Barrera, C.; Esteban, F.; Navarro-Ranninger,
C.; Parra, A.; Aleman, J., Chem. Commun. 2013, 49, 2001-2003;
(h) Gopi, E.; Kumar, T.; Menna-Barreto, R. F.; Valenca, W. O.; da
Silva Junior, E. N.; Namboothiri, I. N., Org. Biomol. Chem. 2015,
13, 9862-9871; (i) Baiju, T. V.; Almeida, R. G.; Sivanandan, S. T.;
de Simone, C. A.; Brito, L. M.; Cavalcanti, B. C.; Pessoa, C.;
Namboothiri, I. N. N.; da Silva Junior, E. N., Eur. J. Med. Chem.
2018, 151, 686-704.
Notes and references
1.
(a) Peterson, E. A.; Overman, L. E., Proc. Natl. Acad. Sci. USA.
2004, 101, 11943-11948; (b) Liu, Y.; Han, S.-J.; Liu, W.-B.;
Stoltz, B. M., Accounts Chem. Res. 2015, 48, 740-751; (c)
Buschleb, M.; Dorich, S.; Hanessian, S.; Tao, D.; Schenthal, K.
B.; Overman, L. E., Angew. Chem. Int. Ed. Engl. 2016, 55, 4156-
86; (d) Ostby, J.; Kelce, W. R.; Lambright, C.; Wolf, C. J.; Mann,
P.; Gray, L. E., Jr., Toxicol. Ind. Health. 1999, 15, 80-93; (e)
Verdisson, S.; Couderchet, M.; Vernet, G., Chemosphere. 2001,
44, 467-474; (f) Verbitski, S. M.; Mayne, C. L.; Davis, R. A.;
Concepcion, G. P.; Ireland, C. M., J. Org. Chem. 2002, 67, 7124-
7126; (g) Li, P.; Huang, W.; Zhuo, J.; Guo, Z.; Cao, W.; Xu, L.;
Ma, L.; Chen, Z.-E.; Kennelly, E. J.; Wu, S.-B.; Long, C.,
Tetrahedron 2015, 71, 5308-5314; (h) Gerry, C. J.; Hua, B. K.;
Wawer, M. J.; Knowles, J. P.; Nelson, S. D., Jr.; Verho, O.;
Dandapani, S.; Wagner, B. K.; Clemons, P. A.; Booker-Milburn,
K. I.; Boskovic, Z. V.; Schreiber, S. L., J. Am. Chem. Soc. 2016,
138, 8920-89277; (i) Tomigahara, Y.; Tarui, H.; Matsui, M.;
Kurosawa, M.; Kawamura, S.; Isobe, N., J. Pestic. Sci. 2018, 43,
114-123.
8.
2.
(a) Marigo, M.; Bachmann, S.; Halland, N.; Braunton, A.;
Jorgensen, K. A., Angew. Chem. Int. Ed. Engl. 2004, 43, 5507-
5510; (b) Smith, A. M.; Hii, K. K., Chem. Rev. 2011, 111, 1637-
1656; (c) Chung, W. J.; Vanderwal, C. D., Angew. Chem. Int. Ed.
Engl. 2016, 55, 4396-434; (d) Petrone, D. A.; Ye, J.; Lautens, M.,
Chem. Rev. 2016, 116, 8003-104; (e) Agarwal, V.; Miles, Z. D.;
Winter, J. M.; Eustaquio, A. S.; El Gamal, A. A.; Moore, B. S.,
Chem. Rev. 2017, 117, 5619-5674; (f) Egorin, M. J.; Rosen, D.
M.; Benjamin, S. E.; Callery, P. S.; Sentz, D. L.; Eiseman, J. L.,
Cancer Chemoth. Pharm. 1997, 41, 9-14; (g) Singh, S.; Mann, B.
K., Clin. Cosmet. Investig. Dermatol. 2012, 5, 61-68; (h) Teasdale,
M. E.; Prudhomme, J.; Torres, M.; Braley, M.; Cervantes, S.;
Bhatia, S. C.; La Clair, J. J.; Le Roch, K.; Kubanek, J., ACS Med.
Chem. Lett. 2013, 4, 989-993;
9.
3.
(a) Gardi, R.; Vitali, R.; Falconi, G.; Ercoli, A., J. Med. Chem.
1972, 15, 556-558; (b) Joselevich, M.; Ghini, A. A.; Burton, G.,
Org. Biomol. Chem. 2003, 1, 939-943; (c) Jung, S. H.; Hwang, G.
S.; Lee, S. I.; Ryu, J. Org. Chem. 2012, 77, 2513-2518; (d)
Senczyszyn, J.; Brice, H.; Clayden, J., Org. Lett. 2013, 15, 1922-
1925; (e) Liu, Y.-L.; Liao, F.-M.; Niu, Y.-F.; Zhao, X.-L.; Zhou,
J., Org. Chem. Front. 2014, 1; (f) Bao, X.; Wang, B.; Cui, L.; Zhu,
G.; He, Y.; Qu, J.; Song, Y., Org. Lett. 2015, 17, 5168-5171; (g)
Shim, S. Y.; Kim, J. Y.; Nam, M.; Hwang, G. S.; Ryu, D. H., Org.
Lett. 2016, 18, 160-163; (h) Martinez, L. P.; Umemiya, S.;
Wengryniuk, S. E.; Baran, P. S., J. Am. Chem. Soc. 2016, 138,
7536-7539; (i) Juhl, K.; Fjelbye, K.; Marigo, M.; Clausen, R.,
Synlett 2016, 28, 425-428; (j) Fjelbye, K.; Marigo, M.; Clausen, R.
P.; Juhl, K., Org. Lett. 2016, 18, 1170-1173; (k) Sun, B.; Jin, C.;
Su, W., J. Chem. Res. 2016, 40, 407-409; (l) Essiz, S.; Dalkilic,
E.; Sari, O.; Dastan, A.; Balci, M., Tetrahedron 2017, 73, 1640-
1649;
10. (a) Singh, J.; Petter, R. C.; Baillie, T. A.; Whitty, A., Nat. Rev.
Drug. Discov. 2011, 10, 307-317; (b) Bauer, R. A., Drug. Discov.
Today. 2015, 20, 1061-1073; (c) Lonsdale, R.; Ward, R. A., Chem.
Soc. Rev. 2018, 47, 3816-3830.
11. (a) Ostrem, J. M.; Peters, U.; Sos, M. L.; Wells, J. A.; Shokat, K.
M., Nature 2013, 503, 548-551; (b) Lim, S. M.; Westover, K. D.;
Ficarro, S. B.; Harrison, R. A.; Choi, H. G.; Pacold, M. E.;
Carrasco, M.; Hunter, J.; Kim, N. D.; Xie, T.; Sim, T.; Janne, P.
A.; Meyerson, M.; Marto, J. A.; Engen, J. R.; Gray, N. S., Angew.
Chem. Int. Ed. Engl. 2014, 53, 199-204; (c) Shibata, Y.; Chiba,
M., Drug. Metab. Dispos. 2015, 43, 375-384; (d) Barf, T.; Covey,
(m) Shi, H.; Michaelides, I. N.; Darses, B.; Jakubec, P.; Nguyen,
Q. N. N.; Paton, R. S.; Dixon, D. J., J. Am. Chem. Soc. 2017, 139,
17755-17758; (n) Balaraman, K.; Ding, R.; Wolf, C., Adv. Synth.