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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Letter Article

Enantioselective Synthesis of Coumarins Catalyzed by Chiral Squaramide

Author(s): Zhijing Liu, Zhiwei Ma*, Chuanchuan Wang, Degang Ding, Juntao Liu, Xiaopei Chen and Guangwei Geng

Volume 19, Issue 11, 2022

Published on: 19 April, 2022

Page: [919 - 923] Pages: 5

DOI: 10.2174/1570178619666220309155353

Price: $65

Abstract

A newly chiral tertiary amine-squaramide has successfully developed and applied into the asymmetric Michael addition of 4-hydroxycoumarin to β,γ-unsaturated α-ketoesters. The catalyst system performed well with a low catalyst loading of 1 mol% under mild reaction conditions. A series of coumarin derivatives were obtained with good yields and enantioselectivities.

Keywords: Coumarin derivatives, Michael addition, organocatalysis, squaramides, β, γ-unsaturated α-ketoesters, 4-hydroxycoumarin.

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[1]
Keri, R.S. B.S.S.; Nagaraja, B.M.; Santos, M.A. Eur. J. Med. Chem., 2015, 100, 257-269.
[http://dx.doi.org/10.1016/j.ejmech.2015.06.017] [PMID: 26112067]
[2]
Kasperkiewicz, K.; Ponczek, M.B.; Owczarek, J.; Guga, P.; Budzisz, E. Molecules, 2020, 25(6), 1465.
[http://dx.doi.org/10.3390/molecules25061465] [PMID: 32213944]
[3]
Nisha, H.; Dheeraj, B.; Rupali, B. K.D.P.; Rekha, B. World J. Pharm. Res., 2021, 10(2), 234-246.
[4]
Ligia, S.S.P.; Mara, R.C.C.; Marcus, V.N.S. Curr. Org. Synth., 2018, 15(1), 21-37.
[http://dx.doi.org/10.2174/1570179414666170614124053]
[5]
Maja, M.; Melita, L.; Marija, K. Curr. Org. Chem., 2020, 24(1), 4-43.
[http://dx.doi.org/10.2174/1385272824666200120144305]
[6]
Komal, C.; Jeevan Lal, P.; Mahapatra, S.P.; Santhosh, P. Curr. Org. Chem., 2020, 24(22), 2601-2611.
[http://dx.doi.org/10.2174/1385272824999201013164825]
[7]
Desimoni, G.; Faita, G.; Quadrelli, P. Chem. Rev., 2013, 113(8), 5924-5988.
[http://dx.doi.org/10.1021/cr4000732] [PMID: 23750879]
[8]
Halland, N.; Velgaard, T.; Jørgensen, K.A. J. Org. Chem., 2003, 68(13), 5067-5074.
[http://dx.doi.org/10.1021/jo0343026] [PMID: 12816459]
[9]
Calter, M.A. Wang. J. Org. Lett., 2009, 11(10), 2205-2208.
[http://dx.doi.org/10.1021/ol900586f] [PMID: 19366193]
[10]
Gao, Y.; Ren, Q.; Wang, L. Wang. J. Chemistry, 2010, 16(44), 13068-13071.
[http://dx.doi.org/10.1002/chem.201002202] [PMID: 21031372]
[11]
Chen, X-K.; Zheng, C-W.; Zhao, S-L.; Chai, Z.; Yang, Y-Q.; Zhao, G.; Cao, W-G. Adv. Synth. Catal., 2010, 352(10), 1648-1652.
[http://dx.doi.org/10.1002/adsc.201000045]
[12]
Xu, D-Q.; Wang, Y-F.; Zhang, W.; Luo, S-P.; Zhong, A-G.; Xia, A-B.; Xu, Z-Y. Chemistry, 2010, 16(14), 4177-4180.
[http://dx.doi.org/10.1002/chem.201000094] [PMID: 20229539]
[13]
Wang, Y-F.; Wang, K.; Zhang, W.; Zhang, B-B.; Zhang, C-X.; Xu, D-Q. Eur. J. Org. Chem., 2012, 2012(19), 3691-3696.
[http://dx.doi.org/10.1002/ejoc.201200179]
[14]
Rong, C.; Pan, H.; Liu, M.; Tian, H.; Shi, Y. Chemistry, 2016, 22(9), 2887-2891.
[http://dx.doi.org/10.1002/chem.201503327] [PMID: 26663588]
[15]
Dajek, M. Pruszczyńska, A.; Konieczny, K.A.; Kowalczyk, R. Adv. Synth. Catal., 2020, 362(17), 3613-3620.
[http://dx.doi.org/10.1002/adsc.202000455]
[16]
Dong, Z.; Feng, J.; Fu, X.; Liu, X.; Lin, L.; Feng, X. Chemistry, 2011, 17(4), 1118-1121.
[http://dx.doi.org/10.1002/chem.201002687] [PMID: 21243677]
[17]
Liu, S.; Xu, Z-H.; Wang, X.; Zhu, H-R.; Wang, M-C. J. Org. Chem., 2019, 84(21), 13881-13889.
[http://dx.doi.org/10.1021/acs.joc.9b02046] [PMID: 31536355]
[18]
Ian Storer, R.; Aciro, C.; Jones, L.H. Chem. Soc. Rev., 2011, 40(5), 2330-2346.
[http://dx.doi.org/10.1039/c0cs00200c] [PMID: 21399835]
[19]
Malerich, J.P.; Hagihara, K.; Rawal, V.H. J. Am. Chem. Soc., 2008, 130(44), 14416-14417.
[http://dx.doi.org/10.1021/ja805693p] [PMID: 18847268]
[20]
Chauhan, P.; Mahajan, S.; Kaya, U.; Hack, D.; Enders, D. Adv. Synth. Catal., 2015, 357(2-3), 253-281.
[http://dx.doi.org/10.1002/adsc.201401003]
[21]
Abdul, R.; Cihangir, T. Curr. Org. Chem., 2016, 20(28), 2996-3013.
[http://dx.doi.org/10.2174/1385272820666160805113749]
[22]
Phillips, A.M.F.; Prechtl, M.H.G.; Pombeiro, A.J.L. Catalysts, 2021, 11(5), 569.
[http://dx.doi.org/10.3390/catal11050569]
[23]
Ma, Z-W.; Liu, Y-X.; Zhang, W-J.; Tao, Y.; Zhu, Y.; Tao, J-C.; Tang, M-S. Eur. J. Org. Chem., 2011, 2011(33), 6747-6754.
[http://dx.doi.org/10.1002/ejoc.201101086]
[24]
Ma, Z.; Liu, Y.; Li, P.; Ren, H.; Zhu, Y.; Tao, J. Tetrahedron Asymmetry, 2011, 22(18), 1740-1748.
[http://dx.doi.org/10.1016/j.tetasy.2011.10.002]
[25]
Song, Z-T.; Zhang, T.; Du, H-L.; Ma, Z-W.; Zhang, C-H.; Tao, J-C. Chirality, 2014, 26(2), 121-127.
[http://dx.doi.org/10.1002/chir.22279] [PMID: 24420919]
[26]
Ma, Z.; Liu, Y.; Huo, L.; Gao, X.; Tao, J. Tetrahedron Asymmetry, 2012, 23(6), 443-448.
[http://dx.doi.org/10.1016/j.tetasy.2012.03.020]
[27]
Ma, Z.; Wu, Y.; Sun, B.; Du, H.; Shi, W.; Tao, J. Tetrahedron Asymmetry, 2013, 24(1), 7-13.
[http://dx.doi.org/10.1016/j.tetasy.2012.11.009]
[28]
Ma, Z-W.; Liu, X-F.; Sun, B.; Huang, X-H.; Tao, J-C. Synthesis, 2017, 49(06), 1307-1314.
[http://dx.doi.org/10.1055/s-0036-1588090]
[29]
Ma, Z.; Liu, X.; Liu, J.; Liu, Z.; Tao, J. Tetrahedron Lett., 2017, 58(48), 4487-4490.
[http://dx.doi.org/10.1016/j.tetlet.2017.10.026]
[30]
Ma, Z. L, X.; Juntao, L.; Jingchao, T. Youji Huaxue, 2018, 38(1), 183-189.
[http://dx.doi.org/10.6023/cjoc201706025]
[31]
Zhu, Y.; Malerich, J.P.; Rawal, V.H. Angew. Chem. Int. Ed., 2010, 49(1), 153-156.
[http://dx.doi.org/10.1002/anie.200904779]

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