Progress in Synthesis of Nitrogen Heterocycles Catalyzed by Chiral Phosphine

doi:10.6023/cjoc202208024

Abstract

Chiral aza-heterocycles are important molecular skeletons of organic chemistry, which are extensively found in pharmaceuticals, pesticides and biologically active natural products. As a significant organic chemistry research filed, the development of efficient novel synthetic methods of them has been a challenge. Among these strategies for the synthesis of aza-heterocycles compounds, chiral phosphine organocatalysis provides a practical and powerful platform. The recent progress in synthesis of chiral nitrogen heterocycles catalyzed by chiral phosphine is summarized, and the development of this field is also prospected.

Key words: chiral phosphine catalyst, organocatalysis, annulation reaction, chiral N-heterocycle

Cite this article

Hongxia Ren, Mengmeng Ma, You Huang. Progress in Synthesis of Nitrogen Heterocycles Catalyzed by Chiral Phosphine[J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3129-3142.

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Fig. & Tab. 33

Scheme 1. Chiral phosphine catalyzed [2+2] annulations of ketenes with N-Ts imines

Scheme 2. Chiral phosphine catalyzed [3+2] annulations of imines with allenoates

Scheme 3. Chiral phosphinothiourea catalyzed [3+2] annulations of imines

Scheme 4. Chiral acid-base phosphine catalyzed aza-MBH domino reaction of alkenes and N-tosylimines

Scheme 5. Chiral phosphine catalyzed [3+2] annulations of allenes with imines for synthesis precursors of natural products

Scheme 6. Phosphine catalyzed intramolecular γ-addition of nitrogen nucleophiles

Scheme 7. Bifunctional phosphine catalyzed [3+2] annuluations reaction of cyclic imines

Scheme 8. Hydroxyproline-derived phosphine catalyzed [3+2] annulations reaction

Scheme 9. Spiro chiral phosphine catalyzed [4+1] annulations reaction of β'-acetoxy allenoates and intramolecular [3+2] annulations reaction

Scheme 10. Phosphine catalyzed [3+2] annuluations reaction with ketimines and allenoates

Scheme 11. Phosphine-catalyzed [3+2] annulations reaction and intramolecular Rauhut-Currier reaction

Scheme 12. Phosphine catalyzed [3+2] annulations reaction of allenoates and β-carbonyl amides

Scheme 13. [1+4] annulation of α,β-unsaturated imines with MBH carbonates catalyzed by P-chiral phosphine oxide-phosphine

Scheme 14. Phosphine catalyzed [3+2] annulations reaction of allenoates and N-Ts imines

Scheme 15. Phosphine catalyzed enantioselective [1+4] annulation of MBH carbonates with α,β-unsaturated imines

Scheme 16. Chiral bifunctional bisphosphine catalyzed enantioselective tandem Michael addition of oxindoles and ynones

Scheme 17. Phosphine catalyzed asymmetric cycloaddition reaction of diazenes

Scheme 18. Phosphine catalyzed [8+2] annuluations reaction

Scheme 19. Phosphine catalyzed stereoselective tandem annulation reaction

Scheme 20. Phosphine-catalyzed asymmetric tandem isomerization/annulation of allyl amines with γ-substituted allenoates

Scheme 21. Chiral phosphine catalyzed [4+2] annulation of allenes with imines

Scheme 22. Chiral phosphine catalyzed aza-Rauhut-Currier [4+2] annulation reaction

Scheme 23. Chiral phosphine catalyzed intramolecular [4+2] annulation reaction

Scheme 24. Chiral thiourea-phosphine catalyzed intramolecular [4+2] annulation reaction

Scheme 25. Chiral phosphine catalyzed [4+2] annulation reaction of ketimines and allenes

Scheme 26. Synthesis of six-membered nitrogen heterocycles by chiral phosphine-catalyzed [3+2] annulations reaction

Scheme 27. Chiral phosphine catalyzed [3+3] annulation reaction of the MBH carbonates with imines

Scheme 28. Chiral phosphine catalyzed [4+2]/[2+2] cyclizations

Scheme 29. Chiral phosphine catalyzed intramolecular Rauhut-Currier reaction

Scheme 30. Sequential phosphine-catalyzed [4+2] annulation reaction

Scheme 31. Chiral phosphine catalyzed [4+2] annulations reaction

Scheme 32. Chiral phosphine catalyzed [4+3] annulation reaction

Scheme 33. Chiral phosphine catalyzed [4+4] annulations reaction

References 64

[1]	Vitaku, E.; Smith, D. T.; Njardarson, J. T. J. Med. Chem. 2014, 57, 10257. doi: 10.1021/jm501100b pmid: 25255204
[2]	Das, P.; Delost, M. D.; Qureshi, M. H.; Smith, D. T.; Njardarson, J. T. J. Med. Chem. 2019, 62, 4265. doi: 10.1021/acs.jmedchem.8b01610
[3]	Vitaku, E.; Smith, D. T.; Njardarson, J. T. J. Med. Chem. 2014, 57, 10257. doi: 10.1021/jm501100b pmid: 25255204
[4]	Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535. doi: 10.1021/ar000253x
[5]	Ye, L.; Zhou, J.; Tang, Y. Chem. Soc. Rev. 2008, 37, 1140. doi: 10.1039/b717758e
[6]	Fan, Y.; Kwon, O. Chem. Commun. 2013, 49, 11588. doi: 10.1039/c3cc47368f
[7]	Xie, P.; Huang, Y. Eur. J. Org. Chem. 2013, 2013, 6213. doi: 10.1002/ejoc.201300469
[8]	Xie, P.; Huang, Y. Org. Biomol. Chem. 2015, 13, 8578. doi: 10.1039/C5OB00865D
[9]	Guo, H.; Fan, Y. C.; Sun, Z.; Wu, Y.; Kwon, O. Chem. Rev. 2018, 118, 10049. doi: 10.1021/acs.chemrev.8b00081
[10]	Ni, H.; Chan, W. L.; Lu, Y. Chem. Rev. 2018, 118, 9344. doi: 10.1021/acs.chemrev.8b00261
[11]	Li, E.; Huang, Y. Chem. Commun. 2020, 56, 680. doi: 10.1039/C9CC08241G
[12]	Chen, S.; Salo, E.; Wheeler, K.; Kerrigan, N. Org. Lett. 2012, 14, 1784. doi: 10.1021/ol3003783 pmid: 22409456
[13]	Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906. doi: 10.1021/jo00114a048
[14]	Xu, Z.; Lu, X. Tetrahedron Lett. 1997, 38, 3461. doi: 10.1016/S0040-4039(97)00656-4
[15]	Jean, L.; Marinetti, A. Tetrahedron Lett. 2006, 47, 2141. doi: 10.1016/j.tetlet.2006.01.122
[16]	Scherer, A.; Gladysz, J. A. Tetrahedron Lett. 2006, 47, 6335. doi: 10.1016/j.tetlet.2006.07.005
[17]	Fleury-Bregeot, N.; Jean, L.; Retailleau, P.; Marinetti, A. Tetrahedron Lett. 2007, 63, 11920. doi: 10.1016/j.tet.2007.09.022
[18]	Pinto, N.; Fleury-Brégeot, N.; Marinetti, A. Eur. J. Org. Chem. 2009, 2009, 146. doi: 10.1002/ejoc.200800598
[19]	Fang, Y.; Jacobsen, E. N. J. Am. Chem. Soc. 2008, 130, 5660. doi: 10.1021/ja801344w
[20]	Takizawa, S.; Inoue, N.; Hirata, S.; Sasai, H. Angew. Chem., Int. Ed. 2010, 49, 9725. doi: 10.1002/anie.201004547
[21]	Andrews, I. P.; Kwon, O. Chem. Sci. 2012, 3, 2510. pmid: 22798981
[22]	Han, X.; Zhong, F.; Wang, Y.; Lu, Y. Angew. Chem., Int. Ed. 2012, 51, 767. doi: 10.1002/anie.201106672
[23]	Yu, Z.; Jin, Z.; Duan, M.; Bai, R.; Lu, Y.; Lan, Y. J. Org. Chem. 2018, 83, 9729. doi: 10.1021/acs.joc.8b01259
[24]	Cai, L.; Zhang, K.; Kwon, O. J. Am. Chem. Soc. 2016, 138, 3298. doi: 10.1021/jacs.6b00567
[25]	Lundgren, R. J.; Wilsily, A.; Marion, N.; Ma, C.; Chung, Y. K.; Fu, G. C. Angew. Chem., Int. Ed. 2013, 52, 2525. doi: 10.1002/anie.201208957
[26]	Wang, Y. Q.; Zhang, Y.; Dong, H.; Zhang, J.; Zhao, J. Eur. J. Org. Chem. 2013, 2013, 3764. doi: 10.1002/ejoc.201201756
[27]	Yu, H.; Zhang, L.; Yang, Z.; Li, Z.; Zhao, Y.; Xiao, Y.; Guo, H. J. Org. Chem. 2013, 78, 8427. doi: 10.1021/jo401107v
[28]	Henry, C.; Xu, Q.; Fan, Y.; Martin, T.; Belding, L.; Dudding, T.; Kwon, O. J. Am. Chem. Soc. 2014, 136, 11890. doi: 10.1021/ja505592h
[29]	Kramer, S.; Fu, G. C. J. Am. Chem. Soc. 2015, 137, 3803. doi: 10.1021/jacs.5b01944 pmid: 25780940
[30]	Lee, S.; Fujiwara, Y.; Nishiguchi, A.; Kalek, M.; Fu, G. C. J. Am. Chem. Soc. 2015, 137, 4587. doi: 10.1021/jacs.5b01985
[31]	Han, X.; Chan, W.-L.; Yao, W.; Wang, Y.; Lu, Y. Angew. Chem., Int. Ed. 2016, 55, 6492. doi: 10.1002/anie.201600453
[32]	Sankar, M.; Garcia-Castro, M.; Golz, C.; Strohmann, C.; Kumar, K. RSC Adv. 2016, 6, 56537. doi: 10.1039/C6RA12387B
[33]	Sankar, M.; Garcia-Castro, M.; Golz, C.; Strohmann, C.; Kumar, K. Angew. Chem., Int. Ed. 2016, 55, 9709. doi: 10.1002/anie.201603936
[34]	Li, E.; Jin, H.; Jia, P.; Dong, X.; Huang, Y. Angew. Chem., Int. Ed. 2016, 55, 11591. doi: 10.1002/anie.201605189
[35]	Jin, H.; Zhang, Q.; Li, E.; Jia, P.; Li, N.; Huang, Y. Org. Biomol. Chem. 2017, 15, 7097. doi: 10.1039/C7OB01820G
[36]	Xing, J.; Lei, Y.; Gao, Y. N.; Shi, M. Org. Lett. 2017, 19, 2382. doi: 10.1021/acs.orglett.7b00910
[37]	Ni, C.; Chen, J.; Zhang, Y.; Hou, Y.; Wang, D.; Tong, X.; Zhu, S. F.; Zhou, Q. Org. Lett. 2017, 19, 3668. doi: 10.1021/acs.orglett.7b01717
[38]	Li, H.; Luo, J.; Li, B.; Yi, X.; He, Z. Org. Lett. 2017, 19, 5637. doi: 10.1021/acs.orglett.7b02800
[39]	Kitagaki, S.; Nakamura, K.; Kawabata, C.; Ishikawa, A.; Takenaga, N.; Yoshida, K. Org. Biomol. Chem. 2018, 16, 1770. doi: 10.1039/c8ob00248g pmid: 29464253
[40]	Cheng, Y.; Han, Y.; Li, P. Org. Lett. 2017, 19, 4774. doi: 10.1021/acs.orglett.7b02144 pmid: 28846432
[41]	Cong, T.; Wang, H.; Li, X.; Wu, H.; Zhang, J. Chem. Commun. 2019, 55, 9176. doi: 10.1039/C9CC04357H
[42]	Wang, C.; Chen, Y.; Li, J.; Zhou, L.; Wang, B.; Xiao, Y.; Guo, H. Org. Lett. 2019, 21, 7519. doi: 10.1021/acs.orglett.9b02800
[43]	Manzano, R.; Romaniega, A.; Prieto, L.; Díaz, E.; Reyes, E.; Uria, U.; Carrillo, L.; Vicario, J. L. Org. Lett. 2020, 22, 4721. doi: 10.1021/acs.orglett.0c01523 pmid: 32464065
[44]	Dai, Z.; Jin, Z. J.; Su, W.; Zeng, W.; Liu, Z.; Chen, M.; Zhou, Q. Org. Lett. 2020, 22, 7008. doi: 10.1021/acs.orglett.0c02558
[45]	Zhou, L.; Zhang, X.; Wang, Q.; Liu, M.; Wang, W.; Wu, Y.; Chen, L.; Guo, H. Org. Lett. 2021, 23, 9173. doi: 10.1021/acs.orglett.1c03483
[46]	Zhu, X.; Lan, J.; Kwon, O. J. Am. Chem. Soc. 2003, 125, 4716. doi: 10.1021/ja0344009
[47]	Wurz, R. P.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 12234. doi: 10.1021/ja053277d
[48]	Xiao, H.; Chai, Z.; Wang, H.; Wang, X.; Cao, D.; Liu, W.; Lu, Y.; Yang, Y.; Zhao, G. Chem.-Eur. J. 2011, 17, 10562. doi: 10.1002/chem.201100850 pmid: 21853481
[49]	Cowen, B.; Miller, S. J. Am. Chem. Soc. 2007, 129, 10988. doi: 10.1021/ja0734243
[50]	Han, X.; Wang, Y.; Zhong, F.; Lu, Y. J. Am. Chem. Soc. 2011, 133, 1726. doi: 10.1021/ja1106282
[51]	Shi, Z.; Tong, Q.; Leong, W.; Zhong, G. Chem.-Eur. J. 2012, 18, 9802. doi: 10.1002/chem.201201318
[52]	Shi, Z.; Yu, P.; Loh, T.; Zhong, G. Angew. Chem., Int. Ed. 2012, 51, 7825. doi: 10.1002/anie.201203316
[53]	Jin, Z.; Yang, R.; Tiwari, B.; Ganguly, R.; Chi, Y. Org. Lett. 2012, 14, 3226. doi: 10.1021/ol3013588
[54]	Zhang, X.; Chen, G.; Dong, X.; Wei, Y.; Shi, M. Adv. Synth. Catal. 2013, 355, 3351. doi: 10.1002/adsc.201300828
[55]	Takizawa, S.; Arteaga, F. A.; Yoshida, Y.; Suzuki, M.; Sasai, H. Asian J. Org. Chem. 2014, 3, 412. doi: 10.1002/ajoc.201300244
[56]	Yu, H.; Zhang, L.; Li, Z.; Liu, H.; Wang, B.; Xiao, Y.; Guo, H. Tetrahedron 2014, 70, 340. doi: 10.1016/j.tet.2013.11.063
[57]	Zhang, L.; Liu, H.; Qiao, G.; Hou, Z.; Liu, Y.; Xiao, Y.; Guo, H. J. Am. Chem. Soc. 2015, 137, 4316. doi: 10.1021/jacs.5b01138 pmid: 25799312
[58]	Zhou, L.; Yuan, C.; Zhang, C.; Zhang, L.; Gao, Z.; Wang, C.; Liu, H.; Wu, Y.; Guo, H. Adv. Synth. Catal. 2017, 359, 2316. doi: 10.1002/adsc.201601434
[59]	Wang, Z.; Xu, H.; Su, Q.; Hu, P.; Shao, P.; He, Y.; Lu, Y. Org. Lett. 2017, 19, 3111. doi: 10.1021/acs.orglett.7b01221
[60]	Zhang, X.; Gan, K.; Liu, X.; Deng, Y.; Wang, F.; Yu, K.; Zhang, J.; Fan, C. Org. Lett. 2017, 19, 3207. doi: 10.1021/acs.orglett.7b01331
[61]	Zhang, Q.; Jin, H.; Feng, J.; Zhu, Y.; Jia, P.; Wu, C.; Huang, Y. Org. Lett. 2019, 21, 1407. doi: 10.1021/acs.orglett.9b00130
[62]	Wang, X.; Lu, M.; Su, Q.; Zhou, M.; Addepalli, Y.; Yao, W.; Wang, Z.; Lu, Y. Chem.-Asian J. 2019, 14, 3409. doi: 10.1002/asia.20190110410.1002/asia.201901104
[63]	Yuan, C.; Zhou, L.; Xia, M.; Sun, Z.; Wang, D.; Guo, H. Org. Lett. 2016, 18, 5644. doi: 10.1021/acs.orglett.6b02885
[64]	Ni, H.; Tang, X.; Zheng, W.; Yao, W.; Ullah, N.; Lu, Y. Angew. Chem., Int. Ed. 2017, 56, 14222. doi: 10.1002/anie.201707183

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