Chinese Journal of Organic Chemistry >
Recent Achievements in the Synthesis of Sulfoximine Derivatives
Received date: 2017-10-06
Revised date: 2017-11-29
Online published: 2017-12-15
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21462022, 21672085).
The sulfoximine derivatives are widely known for their potent biological and medicinal activities. Recently, due to the transition-metal catalysis, great advancements have been achieved in the synthesis of sulfoximine derivatives. Utilizing free NH-sulfoximines as the starting materials, various the direct N-H functionalizations can be accomplished, such as alkynylation, alkenylation, alkylation, arylation, etc. In addition, the ortho arene C(sp2)-H activation can also be obtained through C-H activation reaction with the assistance of S=NH as intramolecular directing groups, thus giving varies (hetero)aromatic molecules. N-H and C-H functionalization reactions of sulfoximines were summarized, and the mechanisms of some novel model reactions are also briefly discussed.
Zhou Hao , Chen Zhiyuan . Recent Achievements in the Synthesis of Sulfoximine Derivatives[J]. Chinese Journal of Organic Chemistry, 2018 , 38(4) : 719 -737 . DOI: 10.6023/cjoc201710002
[1] Bentley, H. R.; McDermott, E. E.; Pace, J.; Whitehead, J. K.; Moran, T. Nature 1950, 165, 150.
[2] (a) Langner, M.; Bolm, C. Angew. Chem., Int. Ed. 2004, 43, 5984.
(b) Shen, X.; Zhang, W.; Ni, C.; Gu, Y.; Hu, J. J. Am. Chem. Soc. 2012, 134, 16999.
(c) Harmata, M.; Hong, X. J. Am. Chem. Soc. 2003, 125, 5754.
(d) Koep, S.; Gais, H.-J.; Raabe, G. J. Am. Chem. Soc. 2003, 125, 13243.
(e) Moessner, C.; Bolm, C. Angew. Chem., Int. Ed. 2005, 44, 7564.
[3] Miller, P.; James, G. W. L. Arch. Int. Pharmacodyn. Ther. 1978, 231, 328.
[4] Park, S. J.; Baars, H.; Mersmann, S.; Buschmann, H.; Baron, J. M.; Amann, P. M.; Czaja, K.; Hollert, H.; Bluhm, K.; Redelstein, R.; Bolm, C. ChemMedChem 2013, 8, 217.
[5] Lucking, U.; Jautelat, R.; Kruger, M.; Brumby, T.; Lienau, P.; Schafer, M.; Briem, H.; Schulze, J.; Hillisch, A.; Reichel, A.; Siemeister, G. ChemMedChem 2013, 8, 1021.
[6] Satzinger, G. Drug News Perspect. 2001, 14, 197.
[7] Von Nussbaum, F.; Karthaus, D.; Anlauf, S.; Delbeck, M.; Li, V.; Meibom, D.; Lustig, K.; Schneider, D. WO 2010115548, 2010.
[8] Walker, D.; Zawistoski, M.; McGlynn, M.; Li, J.; Kung, D. W.; Bonnette, P.; Baumann, A.; Buckbinder, L.; Houser, J. A.; Boer, J.; Mistry, A.; Han, S.; Xing, L.; Perez, A. B. Bioorg. Med. Chem. Lett. 2009, 19, 3253.
[9] Ulrich, L. Angew. Chem., Int. Ed. 2013, 52, 9399.
[10] (a) Bentley, H. R.; Whitehead, J. K. J. Chem. Soc. 1952, 1572.
(b) Johnson, C. R.; Haake, M.; Schroeck, C. W. J. Am. Chem. Soc. 1970, 92, 6594.
(c) Stoss, P.; Satzinger, G. Angew. Chem., Int. Ed. 1971, 10, 76.
(d) Johnson, C. R.; Schroeck, C. W. J. Am. Chem. Soc. 1973, 95, 7418.
(e) Rynbrandt, R. H.; Balgoyen, D. P. J. Org. Chem. 1978, 43, 1824.
(f) Brandt, J.; Gais, H. J. Tetrahedron:Asymmetry 1997, 8, 909.
[11] (a) Tamura, Y.; Sumoto, K.; Minamikawa, J.; Ikeda, M. Tetrahedron Lett. 1972, 4137.
(b) Tamura, Y.; Minamikawa, J.; Sumoto, K.; Fujii, S.; Ikeda, M. J. Org. Chem. 1973, 38, 1239.
(c) Johnson, C. R.; Kirchhoff, R. A.; Corkins, H. G. J. Org. Chem. 1974, 39, 2458.
(d) Allenmark, S.; Claeson, S.; Lowendahl, C. Tetrahedron:Asymmetry 1996, 7, 361.
[12] (a) Takada, H.; Ohe, K.; Uemura, S. Angew. Chem., Int. Ed. 1999, 38, 1288.
(b) Lacote, E.; Amatore, M.; Fensterbank, L.; Malacria, M. Synlett 2002, 116.
(c) Cren, S.; Kinahan, T. C.; Skinner, C. L.; Tye, H. Tetrahedron Lett. 2002, 43, 2749.
(d) Okamura, H.; Bolm, C. Org. Lett. 2004, 6, 1305.
(e) Cho, G. Y.; Bolm, C. Org. Lett. 2005, 7, 4983.
(f) Mancheno, O. G.; Bolm, C. Org. Lett. 2006, 8, 2349.
(g) Mancheno, O. G.; Dallimore, J.; Plant, A.; Bolm, C. Org. Lett. 2009, 11, 2429.
[13] Miao, J.; Richards, N. G. J.; Ge, H. Chem. Commun. 2014, 50, 9687.
[14] Zenzola, M.; Doran, R.; Degennaro, L.; Luisi, R.; Bull, J. A. Angew. Chem., Int. Ed. 2016, 55, 7203.
[15] Wang, J.; Frings, M.; Bolm, C. Chem.-Eur. J. 2014, 20, 966.
[16] Cheng, Y.; Dong, W.; Wang, L.; Parthasarathy, K.; Bolm, C. Org. Lett. 2014, 16, 2000.
[17] Teng, F.; Cheng, J.; Yu, J.-T. Org. Biomol. Chem. 2015, 13, 9934.
[18] Teng, F.; Sun, S.; Jiang, Y.; Yu, J.-T.; Cheng, J. Chem. Commun. 2015, 51, 5902.
[19] Teng, F.; Cheng, J.; Bolm, C. Org. Lett. 2015, 17, 3166.
[20] Wang, H.; Frings, M.; Bolm, C. Org. Lett. 2016, 18, 2431.
[21] Dehli, J. R.; Bolm, C. J. Org. Chem. 2004, 69, 8518.
[22] Chen, X.-Y.; Bohmann, R. A.; Wang, L.; Dong, S.; Räuber, C.; Bolm, C. Chem.-Eur. J. 2015, 21, 10330.
[23] Chen, Z.; Huang, J.; Wang, Z. J. Org. Chem. 2016, 81, 9308.
[24] Wang, L.; Huang, H.; Priebbenow, D. L.; Pan, F.-F.; Bolm, C. Angew. Chem., Int. Ed. 2013, 52, 3478.
[25] Priebbenow, D. L.; Becker, P.; Bolm, C. Org. Lett. 2013, 15, 6155.
[26] Chen, X. Y.; Wang, L.; Frings, M.; Bolm, C. Org. Lett. 2014, 16, 3796.
[27] Wang, H.; Cheng, Y.; Becker, P.; Raabe, G.; Bolm, C. Angew. Chem., Int. Ed. 2016, 55, 12655.
[28] Pirwerdjan, R.; Priebbenow, D. L.; Becker, P.; Lamers, P.; Bolm, C. Org. Lett. 2013, 15, 5397.
[29] Pirwerdjan, R.; Becker, P.; Bolm, C. Org. Lett. 2015, 17, 5008.
[30] Pirwerdjan, R.; Becker, P.; Bolm, C. Org. Lett. 2016, 18, 3307.
[31] Bolm, C.; Hildebrand, J. P. J. Org. Chem. 2000, 65, 169.
[32] Cho, G. Y.; Rémy, P.; Jansson, J.; Moessner, C.; Bolm, C. Org. Lett. 2004, 6, 3293.
[33] Sedelmeier, J.; Bolm, C. J. Org. Chem. 2005, 70, 6904.
[34] Moessner, C.; Bolm, C. Org. Lett. 2005, 7, 2667.
[35] Kim, J.; Ok, J.; Kim, S.; Choi, W.; Lee, P. H. Org. Lett. 2014, 16, 4602.
[36] Miyasaka, M.; Hirano, K.; Satoh, T.; Kowalczyk, R.; Bolm, C.; Miura, M. Org. Lett. 2010, 13, 359.
[37] Wang, L.; Priebbenow, D. L.; Dong, W.; Bolm, C. Org. Lett. 2014, 16, 2661.
[38] Aithagani, S. K.; Kumar, M.; Yadav, M.; Vishwakarma, R. A.; Singh, P. P. J. Org. Chem. 2016, 81, 5886.
[39] Aithagani, S. K.; Dara, S.; Munagala, G.; Aruri, H.; Yadav, M.; Singh, P. P. Org. Lett. 2015, 17, 5547.
[40] Priebbenow, D. L.; Bolm, C. Org. Lett. 2014, 16, 1650.
[41] Zou, Y.; Xiao, J.; Peng, Z.; Dong, W.; An, D. Chem. Commun. 2015, 51, 14889.
[42] Qin, W. J.; Li, Y.; Yu, X.; Deng, W.-P. Tetrahedron 2015, 71, 1182.
[43] Dong, S.; Frings, M.; Cheng, H.; Wen, J.; Zhang, D.; Raabe, G.; Bolm, C. J. Am. Chem. Soc. 2016, 138, 2166.
[44] Zhou, H.; Hong, J.; Huang, J.-P.; Chen, Z.-Y. Asian J. Org. Chem. 2017, 6, 817.
[45] Teng, F.; Yu, J. T.; Jiang, Y.; Yang, H.; Cheng, J. Chem. Commun. 2014, 50, 8412.
[46] Hu, W.; Teng, F.; Peng, H.; Yu, J.; Sun, S.; Cheng, J. Shao, Y. Tetrahedron Lett. 2015, 56, 7056.
[47] Teng, F.; Yu, J.-T.; Zhou, Z.; Chu, H.; Cheng, J. J. Org. Chem. 2015, 80, 2822.
[48] Dannenberg, C. A.; Fritze, L.; Krauskopf, F.; Bolm, C. Org. Biomol. Chem. 2017, 15, 1086.
[49] Peng, H.; Yu, J. T.; Bao, W.; Xu, J.; Cheng, J. Org. Biomol. Chem. 2015, 13, 10600.
[50] Bohnen, C.; Bolm, C. Org. Lett. 2015, 17, 3011.
[51] Zhu, H.; Yu, J.-T.; Cheng, J. Chem. Commun. 2016, 52, 11908.
[52] Yadav, M. R.; Rit, R. K.; Sahoo, A. K. Chem.-Eur. J. 2012, 18, 5541.
[53] Rit, R. K.; Yadav, M. R.; Sahoo, A. K. Org. Lett. 2012, 14, 3724.
[54] Rit, R. K.; Yadav, M. R.; Ghosh, K.; Shankar, M.; Sahoo, A. K. Org. Lett. 2014, 16, 5258.
[55] Yadav, M. R.; Rit, R. K.; Sahoo, A. K. Org. Lett. 2013, 15, 1638.
[56] Yadav, M. R.; Rit, R. K.; Shankar, M.; Sahoo, A. K. J. Org. Chem. 2014, 79, 6123.
[57] Yadav, M. R.; Shankar, M.; Ramesh, E.; Ghosh, K.; Sahoo, A. K. Org. Lett. 2015, 17, 1886.
[58] Raghuvanshi, K.; Zell, D.; Ackermann, L. Org. Lett. 2017, 19, 1278.
[59] Shankar, M.; Ghosh, K.; Mukherjee, K.; Rit, R. K.; Sahoo, A. K. Org. Lett. 2016, 18, 6416.
[60] Chinnagolla, R. K.; Vijeta, A.; Jeganmohan, M. Chem. Commun. 2015, 51, 12992.
[61] Huang, J.; Huang, Y.; Wang, T.; Huang, Q.; Wang, Z.; Chen, Z.-Y. Org. Lett. 2017, 19, 1128.
[62] Parthasarathy, K.; Bolm, C. Chem.-Eur. J. 2014, 20, 4896.
[63] Dong, W.; Parthasarathy, K.; Cheng, Y.; Pan, F.; Bolm, C. Chem.-Eur. J. 2014, 20, 15732.
[64] Cheng, Y.; Dong, W.; Wang, H.; Bolm, C. Chem.-Eur. J. 2016, 22, 10821.
[65] Dong, W.; Wang, L.; Parthasarathy, K.; Pan, F.; Bolm, C. Angew. Chem., Int. Ed. 2013, 52, 11573.
[66] Cheng, Y.; Bolm, C. Angew. Chem., Int. Ed. 2015, 127, 12526.
[67] Jeon, W. H.; Son, J. Y.; Kim, J. E.; Lee, P. H. Org. Lett. 2016, 18, 3498.
[68] Wen, J.; Tiwari, D. P.; Bolm, C. Org. Lett. 2017, 19, 1706.
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