Recent Advances of Chiral Hypervalent Iodine Reagents
- Corresponding author: Cai Qian, caiqian@jnu.edu.cn
Citation: Cai Qian, Ma Haowen. Recent Advances of Chiral Hypervalent Iodine Reagents[J]. Acta Chimica Sinica, ;2019, 77(3): 213-230. doi: 10.6023/A18110470
For books, see: (a) Chemistry of Hypervalent Compounds, Ed.: AKiba, K. Y., Wiley-VCH, New York, 1999. (b) Zhdankin, V. V. Hypervalent Iodine Chemistry: Preparation, Structure and Syn-thetic Application of Polyvalent Iodine Compounds, John Wiley & Sons Ltd., New York, 2014. (c) Iodine Chemistry And Applications, Ed.: Kaiho, T., John Wiley & Sons Ltd., New York, 2015. (d) Hypervalent Iodine Chemistry: Modern Developments in Organic Synthesis, Ed.: Wirth, T., Springer, 2003.
For recent reviews, see: (a) Yoshimura, A.; Zhdankin, V. V. Chem. Rev. 2016, 116, 3328. (b) Duan, Y.; Jiang, S.; Han, Y.; Sun, B.; Zhang, C. Chin. j. Org. Chem. 2016, 36, 1973(in Chinese). (段亚南, 姜山, 韩永超, 孙博, 张弛, 有机化学, 2016, 36, 1973. ) (c) Ma, J.; Chen, L.; Yuan, Z.; Cheng, H. Chin. j. Org. Chem. 2018, 38, 1586(in Chinese). (马姣丽, 陈立成, 袁中文, 程辉成, 有机化学, 2018, 38, 1586. )
For selected recent reviews, see: (a) Flores, A.; Cots, E.; Bergès, J.; Muñiz, K. Adv. Synth. Catal. 2019, 361, DOI: 10.1002/adsc. 201800521. (b)MartínRomero,R.; Wöste,T. H.; Muñiz,K. Chem. AsianJ. 2014,9,972. (c)Singh,F. V.; Wirth,T. Chem. AsianJ. 2014,9,950. (d)Harned,A. M. TetrahedronLett. 2014,55,4681. (e)Parra,A.; Reboredo, S. Chem. Eur. J. 2013,19,17244.
Liang, H.; Ciufolini, M. A. Angew. Chem. Int. Ed. 2011, 50, 11849.
doi: 10.1002/anie.v50.50
Ochiai, M.; Takeuchi, Y.; Katayama, T.; Sueda, T.; Miyamoto, K. j. Am. Chem. Soc. 2005, 127, 12244. (b) Dohi, T.; Maruyama, A.; Yoshimura, M.; Morimoto, K.; Tohma, H.; Kita, Y. Angew. Chem. Int. Ed. 2005, 44, 6193.
Pribram, R. Justus Liebigs Ann. Chem. 1907, 351, 481.
doi: 10.1002/(ISSN)1099-0690
Imamoto, T.; Koto, H. Chem. Lett. 1986, 967.
Hatzigrigoriou, E.; Varvoglis, A.; Bakola-Christianopoulou, M. j. Org. Chem. 1990, 55, 315.
doi: 10.1021/jo00288a053
Xia, M.; Chen, Z.-C. Synth. Commun. 1997, 27, 1321.
doi: 10.1080/00397919708006060
Ray Ⅲ, D. G.; Koser, G. F. j. Am. Chem. Soc. 1990, 112, 5672.
doi: 10.1021/ja00170a059
Ray Ⅲ D. G.; Koser, G. F. j. Org. Chem. 1992, 57, 1607.
doi: 10.1021/jo00031a054
Tohma, H.; Takizawa, S.; Watanabe, H.; Fukuoka, Y.; Maegawa, T.; Kita, Y. j. Org. Chem. 1999, 64, 3519.
doi: 10.1021/jo982295t
Rabah, G. A.; Koser, G. F. Tetrahedron Lett. 1996, 37, 6453.
doi: 10.1016/0040-4039(96)01436-0
(a) Wirth, T.; Hirt, U. H. Tetrahedron Asymmetry 1997, 8, 23. (b) Hirt, U. H.; Spingler, B.; Wirth, T. j. Org. Chem. 1998, 63, 7674. (c) Hirt, U. H.; Schuster, M. F. H.; French, A. N.; Wiest, O. G.; Wirth, T. Eur. j. Org. Chem. 2001, 1569.
Mizar, P.; Laverny, A.; EI-Sherbini, M.; Farid, U.; Brown, M.; Malmedy, F.; Wirth, T. Chem. Eur. j. 2014, 20, 9910.
doi: 10.1002/chem.201403891
Hempel, C.; Maichle-Mössmer, C.; Pericàs, M. A.; Nachtsheim, B. j. Adv. Synth. Catal. 2017, 359, 2941.
Fujita, M.; Okuno, S.; Lee, H. J.; Sugimura, T.; Okuyama, T. Tetrahedron Lett. 2007, 48, 8691.
doi: 10.1016/j.tetlet.2007.10.015
(a) Uyanik, M.; Yasui, T.; Ishihara, K. Angew. Chem. Int. Ed. 2010, 49, 2175. (b) Uyanik, M.; Yasui, T.; Ishihara, K. Tetrahedron 2010, 66, 5841.
(a) Fujita, M.; Yoshida, Y.; Miyata, K.; Wakisaka, A.; Sugimura, T. Angew. Chem. Int. Ed. 2010, 49, 7068. (b) Fujita, M.; Mori, K.; Shimogaki, M.; Sugimura, T. Org. Lett. 2012, 14, 1294. (c) Shimogaki, M.; Fujita, M.; Sugimura, T. Eur. j. Org. Chem. 2013, 7128. (d) Takesue, T.; Fujita, M.; Sugimura, T.; Akutsu, H. Org. Lett. 2014, 16, 4634.
Fujita, M.; Wakita, M.; Sugimura, T. Chem. Commun. 2011, 47, 3983.
doi: 10.1039/c1cc10129c
(a) Shimogaki, M.; Fujita, M.; Sugimura, T. Angew. Chem. Int. Ed. 2016, 55, 15797. (b) Shimogaki, M.; Fujita, M.; Sugimura, T. j. Org. Chem. 2017, 82, 11836.
Röben, C.; Souto, j. A.; González, Y.; Lishchynskyi, A.; Muñiz, K. Angew. Chem. Int. Ed. 2011, 50, 9478.
doi: 10.1002/anie.v50.40
Muñiz, K.; Barreiro, L.; Romero, R. M.; Martínez, C. j. Am. Chem. Soc. 2017, 139, 4354.
doi: 10.1021/jacs.7b01443
(a) Haubenreisser, S.; Wöste, T. H.; Martínez, C.; Ishihara, K.; Muñiz, K. Angew. Chem. Int. Ed. 2016, 55, 413. (b) Wöste, T. H.; Muñiz, K. Synthesis 2016, 48, 816.
(a) Farid, U.; Wirth, T. Angew. Chem. Int. Ed. 2012, 51, 3462. (b) Mizar, P.; Niebuhr, R.; Hutchings, M.; Farooq, U.; Wirth, T. Chem. Eur. J. 2016, 22, 1614.
Gelis, C.; Dumoulin, A.; Bekkaye, M.; Neuville, L.; Masson, G. Org. Lett. 2017, 19, 278.
doi: 10.1021/acs.orglett.6b03631
(a) Kong, W.; Feige, P.; de Haro, T.; Nevado, C. Angew. Chem. Int. Ed. 2013, 52, 2469. (b) Pluta, R.; Krach, P. E.; Cavallo, L.; Falivene, L.; Rueping, M. ACS Catal. 2018, 8, 2582.
Wu, H.; He, Y.-P.; Xu, L.; Zhang, D.-Y.; Gong, L.-Z. Angew. Chem. Int. Ed. 2014, 53, 3466.
doi: 10.1002/anie.201309967
Zhang, D.-Y.; Xu, L.; Wu, H.; Gong, L.-Z. Chem. Eur. j. 2015, 21, 10314.
doi: 10.1002/chem.201501583
Cao, Y.; Zhang, X.; Lin, G.; Zhang-Negrerie, D.; Du, Y. Org. Lett. 2016, 18, 5580.
doi: 10.1021/acs.orglett.6b02816
Farid, U.; Malmedy, F.; Claveau, R.; Albers, C.; Wirth, T. Angew. Chem. Int. Ed. 2013, 52, 7018.
doi: 10.1002/anie.201302358
Brown, M.; Kumar, R.; Rehbein, J.; Wirth, T. Chem. Eur. j. 2016, 22, 4030.
doi: 10.1002/chem.201504844
Banik, S. M.; Medley, j. W.; Jacobsen, E. N. j. Am. Chem. Soc. 2016, 138, 5000.
doi: 10.1021/jacs.6b02391
Banik, S. M.; Medley, j. W.; Jacobsen, E. N. Science 2016, 353, 51.
doi: 10.1126/science.aaf8078
Zhou, B.; Haj, M. K.; Jacobsen, E. N.; Houk, K. N.; Xue, X.-S. j. Am. Chem. Soc. 2018, 140, 15206.
doi: 10.1021/jacs.8b05935
Mennie, K. M.; Banik, S. M.; Reichert, E. C.; Jacobsen, E. N. j. Am. Chem. Soc. 2018, 140, 4797.
doi: 10.1021/jacs.8b02143
Qurban, J.; Elsherbini, M.; Wirth, T. j. Org. Chem. 2017, 82, 11872.
doi: 10.1021/acs.joc.7b01571
Hashimoto, T.; Shimazaki, Y.; Omatsu, Y.; Maruoka, K. Angew. Chem. Int. Ed. 2018, 57, 7200.
doi: 10.1002/anie.v57.24
Zhdandin, V. V.; Smart, j. T.; Zhao, P.; Kiprof, P. Tetrahedron Lett. 2000, 41, 5299.
doi: 10.1016/S0040-4039(00)00836-4
Ladziata, U.; Carlson, J.; Zhdankin, V. V. Tetrahedron Lett. 2006, 47, 6301.
doi: 10.1016/j.tetlet.2006.06.103
Altermann, S. M.; Richardson, R. D.; Page, T. K.; Schmidt, R. K.; Holland, E.; Mohammed, U.; Paradine, S. M.; French, A. N.; Richter, C.; Bahar, A. M.; Witulski, B.; Wirth, T. Eur. j. Org. Chem. 2008, 5315.
Farooq, U.; Schäfer, S.; Ali Shah, A.-U.-H.; Freudendahl, D. M.; Wirth, T. Synthesis 2010, 1023.
Volp, K. A.; Harned, A. M. Chem. Commun. 2013, 49, 3001.
doi: 10.1039/c3cc00013c
Boppisetti, j. K.; Birman, V. B. Org. Lett. 2009, 6, 1221.
Guilbault, A.-A.; Basdevant, B.; Wanie, V.; Legault, C. Y. j. Org. Chem. 2012, 77, 11283.
doi: 10.1021/jo302393u
Rodríguez, A.; Moran, W. j. Synthesis 2012, 44, 1178.
doi: 10.1055/s-0031-1290590
Uyanik, M.; Yasui, T.; Ishihara, K. Angew. Chem. Int. Ed. 2013, 52, 9215.
doi: 10.1002/anie.201303559
Uyanik, M.; Sasakura, N.; Mizuno, M.; Ishihara, K. ACS Catal. 2017, 7, 872.
doi: 10.1021/acscatal.6b03380
Uyanik, M.; Yasui, Y.; Ishihara, K. j. Org. Chem. 2017, 82, 11946.
doi: 10.1021/acs.joc.7b01941
Jain, N.; Xu, S.; Ciufolini, M. A. Chem. Eur. j. 2017, 23, 4542.
doi: 10.1002/chem.201700667
Molnár, I. G.; Gilmour, R. j. Am. Chem. Soc. 2016, 138, 5004.
doi: 10.1021/jacs.6b01183
Scheidt, F.; Schäfer, M.; Sarie, j. C.; Doniliuc, C. G.; Molloy, j. J.; Gilmour, R. Angew. Chem. Int. Ed. 2018, 57, 16431.
doi: 10.1002/anie.201810328
Ochiai, M.; Takaoka, Y.; Masaki, Y. j. Am. Chem. Soc. 1990, 112, 5677.
doi: 10.1021/ja00170a063
Ochiai, M.; Kitagawa, Y.; Takayama, N.; Takaoka, Y.; Shiro, M. j. Am. Chem. Soc. 1999, 121, 9234.
Deng, Q.-H.; Wang, j.-C.; Xu, Z.-J.; Zhou, C.-Y.; Che, C.-M. Synthesis 2011, 18, 2959.
Quideau, S.; Lyvinec, G.; Marguerit, M.; Bathany, K.; Ozanne-Beaudenon, A.; Buffeteau, T.; Cavagnat, D.; Chénedé, A. Angew. Chem. Int. Ed. 2009, 48, 4605.
doi: 10.1002/anie.v48:25
Bosset, C.; Coffinier, R.; Peixoto, P. A.; Assal, M. E.; Miqueu, K. M.; Sotiropoulos, j.-M. Pouységu, L.; Quideau, S. Angew. Chem. Int. Ed. 2014, 53, 9860.
doi: 10.1002/anie.201403571
Companys, S.; Peixoto, P. A.; Bosset, C.; Chassaing, S.; Miqueu, K.; Sotiropoulos, j.-M.; Pouységu, L.; Quideau, S. Chem. Eur. j. 2017, 23, 13309.
doi: 10.1002/chem.v23.54
(a) Brenet, S.; Berthiol, F.; Einhorn, j. Eur. j. Org. Chem. 2013, 8094. (b) Brenet S.; Minozzi, C.; Clarens, B.; Amiri, L.; Berthiol, F. Synthesis 2015, 47, 3859
Dohi, T.; Sasa, H.; Miyazaki, K.; Fujitake, M.; Takenaga, N.; Kita, Y. j. Org. Chem. 2017, 82, 11954.
doi: 10.1021/acs.joc.7b02037
Levitre, G.; Dumoulin, A.; Retailleau, P.; Panossian, A.; Leroux, F. R.; Masson, G. j. Org. Chem. 2017, 82, 11877.
doi: 10.1021/acs.joc.7b01597
Xue, j.-H.; Zhou, Q.-L. Acta Chim. Sinica 2014, 72, 778(in Chinese).
Dohi, T.; Maruyama, A.; Takenaga, N.; Senami, K.; Minamitsuji, Y.; Fujioka, H.; Caemmerer, S. B.; Kita, Y. Angew. Chem. Int. Ed. 2008, 47, 3787.
doi: 10.1002/(ISSN)1521-3773
Dohi, T.; Takenaga, N.; Nakae, T.; Toyoda, Y.; Yamasaki, M.; Shiro, M.; Fujioka, H.; Maruyama, A.; Kita, Y. j. Am. Chem. Soc. 2013, 135, 4558.
doi: 10.1021/ja401074u
Yu, J.; Cui, J.; Hou, X.-S.; Liu, S.-S.; Gao, W.-C.; Jiang, S.; Tian, J.; Zhang, C. Tetrahedron: Asymmetry 2011, 22, 2039.
doi: 10.1016/j.tetasy.2011.12.003
Ding, Q.; He, H.; Cai, Q. Org. Lett. 2018, 20, 4554.
doi: 10.1021/acs.orglett.8b01849
Wang, Y.; Yuan, H.; Lu, H.; Zheng, W.-H. Org. Lett. 2018, 20, 2555.
doi: 10.1021/acs.orglett.8b00711
Murray, S. J.; Müller-Bunz, H.; Ibrahim, H. Chem. Commun. 2012, 48, 6268.
doi: 10.1039/c2cc32280c
Ogasawara, M.; Sasa, H.; Hu, H.; Amano, Y.; Nakajima, H.; Takenaga, N.; Nakajima, K.; Kita, Y.; Takahashi, T.; Dohi, T. Org. Lett. 2017, 19, 4102.
doi: 10.1021/acs.orglett.7b01876
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