Recent Advances in Biomimetic Asymmetric Catalysis for Olefin cis-Dihydroxylation

doi:10.6023/cjoc202504015

Abstract

The development of efficient, selective and environmentally friendly catalytic systems for olefin cis-dihydroxylation remains a key objective in synthetic and catalytic chemistry. Naturally occurring Rieske dioxygenases, nonheme iron-dependent enzymes, exemplify this transformation by enabling aerobic, regio-, and stereoselective cis-dihydroxylation of arenes—a critical step in aromatic degradation. These enzymes incorporate both oxygen atoms from O₂ into the cis-dihydrodiol product with high precision. Inspired by the structural and mechanistic features of Rieske dioxygenases, synthetic nonheme iron and manganese complexes have been designed as functional mimics. These complexes effectively mediate asymmetric cis-dihydroxylation of olefins, selectively yielding cis-dihydrodiol products. This review highlights recent progress in bioinspired nonheme iron and manganese complexes for asymmetric cis-dihydroxylation, along with proposed reaction mechanisms.

Key words: biomimetic catalysis, Rieske dioxygenases, asymmetric cis-dihydroxylation, high-valent metal-oxygen species, nonheme metal complexes

Cite this article

Liu Xin, Zheng Shixin, Zhao Huajie, Chen Jie, Wang Bin. Recent Advances in Biomimetic Asymmetric Catalysis for Olefin cis-Dihydroxylation[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202504015.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Kolb H. C.;VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
[2] Heravi M. M.; Zadsirjan V.; Esfandyari M.; Lashaki T. B. Tetrahedron: Asymmetry 2017, 28, 987.
[3] (a) Gao, Y.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 7538.
(b) Kim, B. M.; Sharpless, K. B. Tetrahedron Lett. 1989, 30, 655.
(c) Fleming, P. R.; Sharpless, K. B. J. Org. Chem. 1991, 56, 2869.
(d) Ko, S. Y. J. Org. Chem. 1995, 60, 6250.
(e) Ko, S. Y. J. Org. Chem. 2002, 67, 2689.
[4] (a) Noe, M. C.; Letavic, M. A.; Snow, S. L. In Organic Reactions, Vol. 66, Eds.: Overman, L. E., John Wiley & Sons, Hoboken, NJ, 2005, pp. 109-625.
(b) Tse, M. K.; Schröder, K.; Beller, M. In Modern Oxidation Methods, Eds.: Bäckvall, J.-E., Wiley-VCH, Weinheim, 2011, pp. 1-36.
(c) Martínez, C.; Muñiz, K. In Science of Synthesis: Catalytic Oxidation in Organic Synthesis, Eds.: Muñiz, K., Georg Thieme Verlag KG, Stuttgart, 2018, pp. 309-341.
[5] (a) Zaitsev, A. B.; Adolfsson, H. Synthesis 2006, 11, 1725.
(b) Bataille, C. J. R.; Donohoe, T. J. Chem. Soc. Rev. 2011, 40, 114.
(c) Ottenbacher, R. V.; Talsi, E. P.; Bryliakov, K. P. Russ. Chem. Rev. 2019, 88, 1094.
(d) Achard, T.; Bellemin-Laponnaz, S. Eur. J. Org. Chem. 2021, 2021, 877.
(e) Su, S.; Wang, C. Synthesis 2021, 53, 1229.
[6] Neisius N. M.; Plietker B. J. Org. Chem. 2008, 73, 3218.
[7] Hao B.; Gunaratna M. J.; Zhang M.; Weerasekara S.; Seiwald S. N.; Nguyen V. T.; Meier A.; Hua D. H.J. Am. Chem. Soc. 2016, 138, 16839.
[8] Tian B.; Chen P.; Leng X.; Liu G. Nat.Catal. 2021, 4, 172.
[9] Bhunnoo R. A.; Hu Y.; Lainé D. I.; Brown R. C.D. Angew. Chem., Int. Ed. 2002, 41, 3479.
[10] Wang C.; Zong L.; Tan C.-H.J. Am. Chem. Soc. 2015, 137, 10677.
[11] Karlsson A.; Parales J. V.; Parales R. E.; Gibson D. T.; Eklund H.; Ramaswamy S. Science 2003, 299, 1039.
[12] (a) Özgen, F. F.; Schmidt, S. In Biocatalysis: Enzymatic Basics and Applications, Eds.: Husain, Q.; Ullah, M. F., Springer, Cham, 2019, pp. 57-82.
(b) Guo, Y.; Chang, W.-C.; Li, J.; Davidson, M. In Comprehensive Coordination Chemistry III, third ed, Eds.: Constable, E. C.; Parkin, G.; Que, L., Jr., Elsevier, 2021, pp. 301-332.
[13] (a) Barry, S. M.; Challis, G. L. ACS Catal. 2013, 3, 2362.
(b) Kovaleva, E. G.; Lipscomb, J. D. Nat. Chem. Biol. 2008, 4, 186.
(c) Bugg, T. D. H.; Ramaswamy, S. Curr. Opin. Chem. Biol. 2008, 12, 134.
[14] (a) Sutherlin, K. D.; Rivard, B. S.; Böttger, L. H.; Liu, L. V.; Rogers, M. S.; Srnec, M.; Park, K.; Yoda, Y.; Kitao, S.; Kobayashi, Y.; Saito, M.; Seto, M.; Hu, M.; Zhao, J.; Lipscomb, J. D.; Solomon, E. I. J. Am. Chem. Soc. 2018, 140, 5544.
(b) Rivard, B. S.; Rogers, M. S.; Marell, D. J.; Neibergall, M. B.; Chakrabarty, S.; Cramer, C. J.; Lipscomb, J. D. Biochemistry 2015, 54, 4652.
[15] (a) Neibergall, M. B.; Stubna, A.; Mekmouche, Y.; Münck, E.; Lipscomb, J. D. Biochemistry 2007, 46, 8004.
(b) Wolfe, M. D.; Lipscomb, J. D. J. Biol. Chem. 2003, 278, 829.
[16] (a) Zhu, W.; Kumar, A. Xiong, J. Abernathy, M. J.; Li, X.-X.; Seo, M. S.; Lee, Y.-M.; Sarangi, R.; Guo, Y.; Nam, W. J. Am. Chem. Soc. 2023, 145, 4389.
(b) Zhu, W.; Wu, P.; Larson, V. A.; Kumar, A.; Li, X.-X.; Seo, M. S.; Lee, Y.-M.; Wang, B.; Lehnert, N.; Nam, W. J. Am. Chem. Soc. 2024, 146, 250.
(c) Wu, P.; Zhu, W.; Chen, Y.; Wang, Z.; Kumar, A.; Wang, B.; Nam, W. J. Am. Chem. Soc. 2024, 146, 30231.
[17] (a) Oldenburg, P. D.; Feng, Y.; Pryjomska-Ray, I.; Ness, D.; Que, L., Jr. J. Am. Chem. Soc. 2010, 132, 17713.
(b) Bautz, J.; Comba, P.; Lopez de Laorden, C.; Menzel, M.; Rajaraman, G. Angew. Chem., Int. Ed. 2007, 46, 8067.
(c) Comba, P.; Rajaraman, G.; Rohwer, Heidi. Inorg. Chem. 2007, 46, 3826.
[18] (a) Que, L., Jr.; Tolman, W. B. Nature 2008, 455, 333.
(b) Vicens, L.; Borrell, M.; Costas, M. In Science of Synthesis: Catalytic Oxidation in Organic Synthesis, Eds.: Muñiz, K., Georg Thieme Verlag KG, Stuttgart, 2018, pp. 113-153.
(c) Eisink, N. N. H. M.; Browne, W. R. In Manganese Catalysis in Organic Synthesis, Eds.: Sortais, J.-B., Wiley-VCH, Weinheim, 2021; pp. 323-343.
(d) Talsi, E. P.; Bryliakov, K. P. Coord. Chem. Rev. 2012, 256, 1418.
(e) Sun, W.; Sun, Q. Acc. Chem. Res. 2019, 52, 2370.
(f) Vicens, L.; Olivo, G.; Costas, M. ACS Catal. 2020, 10, 8611.
(g) Xiao, X.; Xu, K.; Gao, Z.-H.; Zhu, Z.-H.; Ye, C.; Zhao, B.; Luo, S.; Ye, S.; Zhou, Y.-G.; Xu, S.; Zhu, S.-F.; Bao, H.; Sun, W.; Wang, X.; Ding, K. Sci. China Chem. 2023, 66, 1553.
(h) Chen, J.; Song, W.; Lee, Y.-M.; Nam, W.; Wang, B. Coord. Chem. Rev. 2023, 477, 214945.
[19] Chen K.; Que, L., Jr. Angew. Chem., Int. Ed. 1999, 38, 2227.
[20] Oldenburg P. D.; Shteinman A. A.; Que, L., Jr. J. Am. Chem. Soc. 2005, 127, 15672.
[21] Ryu J. Y.; Kim J.; Costas M.; Chen K.; Nam W.; Que, L., Jr. Chem. Commun. 2002, 1288.
[22] Costas M.; Tipton A. K.; Chen K.; Jo D.-H.; Que, L., Jr. J. Am. Chem. Soc. 2001, 123, 6722.
[23] Suzuki K.; Oldenburg P. D.; Que, L., Jr. Angew. Chem., Int. Ed. 2008, 47, 1887.
[24] Zang C.; Liu Y.; Xu Z.-J.; Tse C.-W.; Guan X.; Wei J.; Huang J.-S.; Che, C.-M. Angew. Chem., Int. Ed. 2016, 55, 10253.
[25] Cho J.; Jeon S.; Wilson S. A.; Liu L. V.; Kang E. A.; Braymer J. J.; Lim M. H.; Hedman B.; Hodgson K. O.; Valentine J. S.; Solomon E. I.; Nam W. Nature 2011, 478, 502.
[26] Nishikawa Y.; Yamamoto H. J. Am. Chem. Soc. 2011, 133, 8432.
[27] Wei J.; Wu L.; Wang H.-X.; Zhang X.; Tse C.-W.; Zhou C.-Y.; Huang J.-S.; Che, C.-M. Angew. Chem., Int. Ed. 2020, 59, 16561.
[28] Chen J.; Luo X.; Sun Y.; Si S.; Xu Y.; Lee Y.-M.; Nam W.; Wang B. CCS Chem. 2022, 4, 2369.
[29] de Boer, J. W.; Browne, W. R.; Harutyunyan, S. R.; Bini, L.; Tiemersma-Wegman, T. D.; Alsters, P. L.; Hage, R.; Feringa, B. L. Chem. Commun. 2008, 3747.
[30] Chow T. W.-S.; Liu, Y.; Che, C.-M. Chem. Commun. 2011, 47, 11204.
[31] de Boer, J. W.; Browne, W. R.; Brinksma, J.; Alsters, P. L.; Hage, R.; Feringa, B. L. Inorg. Chem. 2007, 46, 6353.
[32] Chen J.; Zhang J.; Sun Y.; Xu Y.; Yang Y.; Lee Y.-M.; Ji W.; Wang B.; Nam W.; Wang B. J. Am. Chem. Soc. 2023, 145, 27626.
[33] (a) Chen, K.; Costas, M.; Kim, J.; Tipton, A. K.; Que, L., Jr. J. Am. Chem. Soc. 2002, 124, 3026.
(b) Feng, Y.; England, J.; Que, L., Jr. ACS Catal. 2011, 1, 1035.
(c) Company, A.; Feng, Y.; Güell, M.; Ribas, X.; Luis, J. M.; Que, L., Jr.; Costas, M. Chem. - Eur. J. 2009, 15, 3359.
[34] (a) Schröder, D.; Shaik, S.; Schwarz, H. Acc. Chem. Res. 2000, 33, 139.
(b) Shaik, S. Isr. J. Chem. 2020, 60, 938.
[35] (a) de Visser, S. P. Chem. - Eur. J. 2020, 26, 5308.
(b) Mukherjee, G.; Satpathy, J. K.; Bagha, U. K.; Mubarak, M. Q. E.; Sastri, C. V.; de Visser, S. P. ACS Catal. 2021, 11, 9761.
[36] (a) Feng, Y.; Ke, C.-y.; Xue, G.; Que, L., Jr. Chem. Commun. 2009, 9, 50.
(b) Choukairi Afailal, N.; Borrell, M.; Cianfanelli, M.; Costas, M. J. Am. Chem. Soc. 2024, 146, 240.

仿生不对称催化烯烃双羟化反应研究进展