Advances of Asymmetric Synthesis Combining of Gold and Chiral Phosphoric Acid Catalysts

doi:10.6023/cjoc202407033

Abstract

Homogeneous gold catalysis has developed rapidly and made great progress in recent years, however, the linear structure of Au(I) complexes and the instability of Au(III) organic complexes limit their application in many asymmetric catalytic reactions. Combining gold with organic small molecules as cocatalysts may promote complementary advantages and greatly expand the application scope of asymmetric gold catalysis. Chiral phosphoric acid is a kind of bifunctional organic catalyst with novel structure. Combining chiral phosphoric acids with transition metals can catalyze many new reactions that are difficult to realize with a single catalyst. The asymmetric reactions catalyzed by gold and chiral phosphoric acid are summarized from three aspects, including counter anion directed catalysis, cooperative catalysis and relay catalysis, as well as the latest research progress and development prospects are also discussed.

Key words: gold catalysis, chiral phosphoric acid, anion directed catalysis, cooperative catalysis, relay catalysis

Cite this article

Xiaoyu Zhu, Shilin Yang, Yiming Luo, Wenze Li. Advances of Asymmetric Synthesis Combining of Gold and Chiral Phosphoric Acid Catalysts[J]. Chinese Journal of Organic Chemistry, 2025, 45(4): 1178-1193.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 41

Scheme 1. Modes of combining metal catalysis and organocatalysis

Scheme 2. Enantioselective cyclization catalyzed by Au(I)- chiral phosphate

Scheme 3. Syntheis of chiral tetrahydrofurans catalyzed by mo- nocationic dinuclear gold complex

Scheme 4. Enantioselective synthesis of methylene pyrrolidines

Scheme 5. Transfer hydrogenation of quinolines catalyzed by chiral gold phosphate

Scheme 6. Enantioselective synthesis of tetrahydroquinoline derivatives

Scheme 7. Au(I) tethered counterion-directed catalytic cascade reaction

Scheme 8. Proposed catalytic mechanism

Scheme 9. Addition of 1-naphthols with allenamides

Scheme 10. Enantioselective synthesis of furoxazines and pyrrolooxazines

Scheme 11. Cascade reactions catalyzed by Au(I)/amine/CPA

Scheme 12. Mannich-type addition of 3-butynols and nitrone

Scheme 13. Proposed cocatalytic mechanism

Scheme 14. Stereoselective oxidative muti-functionalization of terminal alkynes

Scheme 15. Proposed cocatalytic mechanism

Scheme 16. Enantioselective C—H functionalization of toluene

Scheme 17. Enantioselective muti-functionalization of internal alkynes

Scheme 18. Two different catalytic mechanisms

Scheme 19. Intramolecular hydroamination (AuI)/stereocontrolled HEH (CPA) cascade

Scheme 20. Consecutive intramolecular hydroamination (AuI) and stereocontrolled HEH (CPA)

Scheme 21. Proposed relay catalytic mechanism

Scheme 22. Enantioselective synthesis of polycyclic indole derivatives

Scheme 23. Enantioselective synthesis of julolidine derivatives

Scheme 24. Addition of azlactones triggered by cyclization of alkynols

Scheme 25. Proposed catalytic mechanism

Scheme 26. Metal/organo relay catalysis for synthesis of polycyclic compounds

Scheme 27. Reductive hydroamination of terminal alkynes

Scheme 28. Enantioselective synthesis of fused 1,2-dihydroiso-quinolines

Scheme 29. Enantioselective synthesis of tetrahydroquinoline derivatives

Scheme 30. Au(I)/CPA relay catalytic redox-pinacol-Mannich reaction

Scheme 31. Au(I)/CPA relay catalysis for the synthesis of cyclic aminals

Scheme 32. Hydroalkoxylation/Mannich-type/acetalizaion cascade

Scheme 33. Enantioselective synthesis of spiroacetals

Scheme 34. Intramolecular hydroamination/N-sulfonyliminium cyclization cascade

Scheme 35. Application to δ-lactam synthesis

Scheme 36. Enantioselective synthesis of hexahydrofuro[3,2-c]quinolines

Scheme 37. Enantioselective hydroamination/hydroarylation of alkynols

Scheme 38. Enantioselective synthesis of spiroacetals

Scheme 39. Enantioselective synthesis of tetrahydrocarbazole derivatives

Scheme 40. Enantioselective aza-ene-type reactions

Scheme 41. Proposed catalytic mechanism

References 51

[1]	Hashmi, A. S. K.; Hutching, G. J. Angew. Chem., Int. Ed. 2006, 45, 7896.
[2]	Bond, G. C.; Sermon, P. A.; Webb, G.; Buchanan, D. A.; Wells, P. B. J. Chem. Soc., Chem. Commun. 1973, 444.
[3]	Hutchings, G. J. J. Catal. 1985, 96, 292.
[4]	Haruta, M.; Yamada, N.; Kobayashi, T.; Iijima, S. J. Catal. 1989, 115, 301.
[5]	Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405.
[6]	(a) Fukuda, Y.; Utimoto, K.; Nozaki, H. Heterocycles 1987, 25, 297.
	(b) Fukuda, Y.; Utimoto, K. J. Org. Chem. 1991, 56, 3729.
	(c) Fukuda, Y.; Utimoto, K. Bull. Chem. Soc. Jpn. 1991, 64, 2013.
[7]	(a) Teles, J. H.; Brode, S.; Chabanas, M. Angew. Chem., Int. Ed. 1998, 37, 1415.
	(b) Hashimi, A. S. K. Gold Bull. 2004, 37, 51.
[8]	(a) Hashimi, A. S. K. Chem. Rev. 2007, 107, 3180.
	(b) Jimenz-Nunez, E.; Echavarren, A. M. Chem. Commun. 2007, 333.
	(c) Li, Z.; Brouwer, C.; He, C. Chem. Rev. 2008, 108, 3239.
	(d) Arcadi, A. Chem. Rev. 2008, 108, 3266.
	(e) Gorin, D. J.; Sherry, B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351.
[9]	Fürstner, A.; Davies, P. W. Angew. Chem., Int. Ed. 2007, 46, 3410.
[10]	Muñoz, M. P.; Adrio, J.; Carretero, J. C.; Echavarren, A. M. Organometallics 2005, 24, 1293.
[11]	Johansson, M. J.; Gorin, D. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 18002. pmid: 16366541
[12]	(a) Widenhoefer, R. A. Chem. Eur. J. 2008, 14, 5382.
	(b) Sengupta, S.; Shi, X. ChemCatChem 2010, 2, 609.
	(c) Wang, Y.-M.; Lackner, A. D.; Toste, F. D. Acc. Chem. Res. 2014, 47, 889.
	(d) Zi, W.; Dean Toste, F. Chem. Soc. Rev. 2016, 45, 4567.
	(e) Rodriguez, J.; Bourissou, D. Angew. Chem., Int. Ed. 2018, 57, 386.
[13]	(a) Chen, G.-S.; Deng, Y.-J.; Gong, L.-Z.; Mi, A.-Q.; Cui, X.; Jiang, Y.-Z.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2001, 12, 1567. pmid: 11594826
	(b) Nakoji, M.; Kanayama, T.; Okino, T.; Takemoto, Y. Org. Lett. 2001, 3, 3329. pmid: 11594826
[14]	(a) Zhong, C.; Shi, X. Eur. J. Org. Chem. 2010, 2010, 2999.
	(b) Du, Z.; Shao, Z. Chem. Soc. Rev. 2013, 42, 1337.
	(c) Chen, D.-F.; Han, Z.-Y.; Zhou, X.-L.; Gong, L.-Z. Acc. Chem. Res. 2014, 47, 2365.
[15]	Han, Z.-Y.; Wang, C.; Gong, L.-Z. In Science of Synthesis: Asymmetric Organocatalysis, Ed.: Maruoka, K., Vol. 2, Georg Thieme Verlag, Stuttgart, 2012, p. 697.
[16]	Phipps, R. J.; Hamilton, G. L.; Toste, F. D. Nat. Chem. 2012, 4, 603.
[17]	(a) Akiyama, T. Chem. Rev. 2007, 107, 5744.
	(b) Terada, M. Synthesis 2010, 1929.
	(c) Yu, J.; Shi, F.; Gong, L.-Z. Acc. Chem. Res. 2011, 44, 1156.
	(d) Gao, Y.-J.; Yang, L.-H.; Song, S.-J.; Ma, J.-J.; Tang, R.-X.; Bian, R.-H.; Liu, H.-Y.; W, Q.-H.; Wang, C. Chin. J. Org. Chem. 2008, 28, 8 (in Chinese).
	(高勇军, 杨丽华, 宋双居, 马晶军, 唐然肖, 边瑞环, 刘海燕, 吴秋华, 王春, 有机化学, 2008, 28, 8.)
	(e) Su, Y.-J.; Shi, F.-Q. Chin. J. Org. Chem. 2010, 30, 486 (in Chinese).
	(苏亚军, 史福强, 有机化学, 2010, 30, 486.)
[18]	(a) Shao, Z.-H.; Zhang, H.-B. Chem. Soc. Rev. 2009, 38, 2745.
	(b) Wu, X.; Li, M.-L.; Gong, L.-Z. Acta Chim. Sinica 2013, 71, 1091 (in Chinese).
	(吴祥, 李明丽, 龚流柱, 化学学报, 2013, 71, 1091.) doi: 10.6023/A13030279
	(c) Sun, Z.; H, J.-M.; Q, M.-N.; L, K.-S. Chin. J. Org. Chem. 2015, 35, 1250 (in Chinese).
	(孙哲, 何金梅, 屈孟男, 李侃社, 有机化学, 2015, 35, 1250.) doi: 10.6023/cjoc201410014
	(d) Cui, X.-Y.; Zhou, F.; Wu, H.-H.; Zhou, J. Chin. J. Org. Chem. 2022, 42, 3033 (in Chinese).
	(崔效源, 周锋, 吴海虹, 周剑, 有机化学, 2022, 42, 3033.) doi: 10.6023/cjoc202209016
	(e) Xiang, X.; He, Z.-L.; Dong, X.-Q. Chin. J. Org. Chem. 2023, 43, 791 (in Chinese)
	(向勋, 何照林, 董秀琴, 有机化学, 2023, 43, 791). doi: 10.6023/cjoc202211043
[19]	Hamilton, G. L.; Kang, E. J.; Mba, M.; Toste, F. D. Science 2007, 317, 496. pmid: 17656720
[20]	(a) Mayer, S.; List, B. Angew. Chem., Int. Ed. 2006, 45, 4193.
	(b) Zhong, C.; Shi, X.-D. Eur. J. Org. Chem. 2010, 16, 2999.
[21]	Aikawa, K.; Kojima, M.; Mikami, K. Adv. Synth. Catal. 2010, 352, 3131.
[22]	Mourad, A. K.; Leutzow, J.; Czekelius, C. Angew. Chem., Int. Ed. 2012, 51, 11149.
[23]	Tu, X.-F.; Gong, L.-Z. Angew. Chem., Int. Ed. 2012, 51, 1.
[24]	Du, Y.-L.; Hu, Y.; Zhu, Y.-F.; Tu, X.-F.; Han, Z.-Y.; Gong, L.-Z. J. Org. Chem. 2015, 80, 4754.
[25]	Zhang, Z.-H.; Smal, V.; Retailleau, P.; Voituriez, A.; Frison, G.; Marinetti, A.; Guinchard, X. J. Am. Chem. Soc. 2020, 142, 3797.
[26]	Yu, Y.-L.; Zhang, Z.-H.; Voituriez, A.; Rabasso, N.; Frison, G.; Marinetti, A.; Guinchard, X. Chem. Commun. 2021, 57, 10779.
[27]	Zhang, Z.-H.; Sabat, N.; Frison, G.; Marinetti, A.; Guinchard, X. ACS Catal. 2022, 12, 4046.
[28]	Patil, N. T.; Raut, V. S.; Tella, R. B. Chem. Commun. 2013, 49, 570.
[29]	Wei, H.-L.; Bao, M.; Dong, K.-Y.; Qiu, L.-H.; Wu, B.; Hu, W.-H.; Xu, X.-F. Angew. Chem., Int. Ed. 2018, 57, 17200.
[30]	Zhou, S.; Li, Y.-W.; Liu, X.-R.; Hu, W.-H.; Ke, Z.-F.; Xu, X.-F. J. Am. Chem. Soc. 2021, 143, 14703.
[31]	Liu, X.-S.; Tang, Z.-Q.; Zhang, Z.-K.; Zhao, L.; Liu, L. Angew. Chem., Int. Ed. 2022, 61, e202208874.
[32]	Chen, K.-W.; Zhou, S.; Li, C.; Dong, S.-L.; Hong, K.-M.; Xu, X.-F. J. Am. Chem. Soc. 2024, 146, 19261.
[33]	Han, Z.-Y.; Xiao, H.; Chen, X.-H. Gong, L.-Z. J. Am. Chem. Soc. 2003, 131, 9182.
[34]	Liu, X.-Y.; Che, C.-M. Org. Lett. 2009, 11, 4204.
[35]	Muratore, M. E.; Holloway, C. A.; Pilling, A. W.; Storer, R. L.; Trevitt, G.; Dixone, D. J. J. Am. Chem. Soc. 2009, 131, 10796. doi: 10.1021/ja9024885 pmid: 19606900
[36]	Wang, C.; Han, Z.-Y.; Luo, H.-W.; Gong, L.-Z. Org, Lett. 2010, 12, 2266.
[37]	Han, Z.-Y.; Guo, R.; Wang, P.-S.; Chen, D.-F.; Xiao, H.; Gong, L.-Z. Tetrahedron Lett. 2011, 52, 5963.
[38]	Han, Z.-Y.; Chen, D.-F.; Wang, Y.-Y.; Guo, R.; Wang, P.-S.; Wang, C.; Gong, L.-Z. J. Am. Chem. Soc. 2012, 134, 6532.
[39]	Fleischer, S.; Werkmeister, S.; Zhou, S.-L.; Junge, K.; Beller, M. Chem. Eur. J. 2012, 18, 9005.
[40]	Patil, N. T.; Mutyala, A. K.; Konala, A.; Tella, R. B. Chem. Commun. 2012, 48, 3094.
[41]	Liu, X.-Y.; Xiao, Y.-P.; Siu, F.-M.; Ni, L.-C.; Chen, Y.; Wang, L.; Che, C.-M. Org. Biomol. Chem. 2012, 10, 7208.
[42]	Qian, D.-Y.; Zhang, J.-L. Chem.-Eur. J. 2013, 19, 6984.
[43]	He, Y.-P.; Wu, H.; Chen, D.-F.; Yu, J.; Gong, L.-Z. Chem.-Eur. J. 2013, 19, 5232. doi: 10.1002/chem.201300052 pmid: 23512426
[44]	Wu, H.; He, Y.-P.; Gong, L.-Z. Org. Lett. 2013, 15, 460.
[45]	Cala, L.; Mendoza, A.; Fañanás, F. J.; Rodríguez, F. Chem. Commun. 2013, 48, 2715.
[46]	Gregory, A. W.; Jakubec, P.; Turner, P.; Dixon, D. J. Org, Lett. 2013, 15, 4330. doi: 10.1021/ol401784h pmid: 23985045
[47]	Calleja, J.; González-Pérez, A. B.; de Lera, A. R.; Álvarez, R.; Fañanás, F. J.; Rodríguez, F. Chem. Sci. 2014, 5, 996.
[48]	Shinde, V. S.; Mane, M. V.; Vanka, K.; Mallick, A.; Patil, N. T. Chem.-Eur. J. 2014, 20, 1.
[49]	Rexit, A. A.; Mailikezati, M. Tetrahedron Lett. 2015, 56, 2651.
[50]	Zhao, F.; Li, N.; Zhu, Y.-F.; Han, Z.-Y. Org. Lett. 2016, 18, 1506.
[51]	Zhao, F.; Li, N.; Zhang, T.; Han, Z.-Y.; Luo, S.-W.; Gong, L.-Z. Angew. Chem., Int. Ed. 2017, 56, 1.

金和手性磷酸共催化的不对称合成研究进展