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Letters in Organic Chemistry

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

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Short Communication

Amine-Squaramide Catalyzed Asymmetric Michael Addition of Cyclic Diketones and β,γ-unsaturated α-keto Esters

Author(s): Zhi-Jing Liu, Zhi-Wei Ma*, Xiao-Pei Chen, Chuan-Chuan Wang, Jun-Tao Liu and Jing-Chao Tao

Volume 19, Issue 11, 2022

Published on: 29 April, 2022

Page: [1042 - 1046] Pages: 5

DOI: 10.2174/1570178619666220314152530

Price: $65

Abstract

A novel tertiary amine squaramide has been successfully developed and applied to catalyze the asymmetric Michael addition between cyclic diketones and 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 synthetically and pharmaceutically useful chiral bicyclic compounds were obtained with both high yields (up to 97%) and excellent enantioselectivities (up to 97% ee).

Keywords: Michael addition, organocatalysis, tertiary amine-squaramide, cyclic diketone, βγ-unsaturated α-ketoesters, isosteviol derivative.

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[1]
Zhang, Y.; Wang, W. Catal. Sci. Technol., 2012, 2(1), 42-53.
[http://dx.doi.org/10.1039/C1CY00334H]
[2]
Wang, K.; Kong, W. Chin. J. Chem., 2018, 36(3), 247-256.
[http://dx.doi.org/10.1002/cjoc.201700745]
[3]
Das, T.; Mohapatra, S.; Mishra, N.P.; Nayak, S.; Raiguru, B.P. ChemistrySelect, 2021, 6(15), 3745-3781.
[http://dx.doi.org/10.1002/slct.202100679]
[4]
Gangliang, H.; Xue, L. Curr. Org. Synth., 2017, 14(4), 568-571.
[http://dx.doi.org/10.2174/1570179414666161121124846]
[5]
Shagufta, K.; Ameer Fawad, Z.; Sajjad, A.; Rabia, A.; Iqra, K.; Wajiha, Q.; Attia, M. Curr. Org. Chem., 2020, 24(13), 1397-1458.
[http://dx.doi.org/10.2174/1385272824999200616123744]
[6]
Reznikov, A.N.; Klimochkin, Y.N. Synthesis, 2020, 52(06), 781-795.
[http://dx.doi.org/10.1055/s-0039-1690044]
[7]
Péter, B.; Tamás, N.; Zsolt, R.; György, K. Curr. Org. Chem., 2020, 24(7), 746-773.
[http://dx.doi.org/10.2174/1385272824666200316122221]
[8]
Wang, W.; Ye, L.; Shi, Z.; Zhao, Z.; Li, X. RSC Advances, 2018, 8(73), 41699-41704.
[http://dx.doi.org/10.1039/C8RA07809B]
[9]
Singha Roy, S.J.; Mukherjee, S. J. Org. Chem., 2018, 83(19), 12071-12085.
[http://dx.doi.org/10.1021/acs.joc.8b02051] [PMID: 30178668]
[10]
Wang, Q.; Wang, W.; Ye, L.; Yang, X.; Li, X.; Zhao, Z.; Li, X. Molecules, 2017, 22(7), 1096.
[http://dx.doi.org/10.3390/molecules22071096]
[11]
Huang, H.; Kang, J.Y. Org. Lett., 2016, 18(17), 4372-4375.
[http://dx.doi.org/10.1021/acs.orglett.6b02121] [PMID: 27541326]
[12]
Feu, K.S.; Deobald, A.M.; Narayanaperumal, S.; Corrêa, A.G.; Weber Paixão, M. Eur. J. Org. Chem., 2013, 2013(26), 5917-5922.
[http://dx.doi.org/10.1002/ejoc.201300431]
[13]
Ghosh, S.K.; Dhungana, K.; Headley, A.D.; Ni, B. Org. Biomol. Chem., 2012, 10(41), 8322-8325.
[http://dx.doi.org/10.1039/c2ob26248g] [PMID: 22976596]
[14]
Rong, Z-Q.; Jia, M-Q.; You, S-L. Org. Lett., 2011, 13(15), 4080-4083.
[http://dx.doi.org/10.1021/ol201595f] [PMID: 21732659]
[15]
Desimoni, G.; Faita, G.; Quadrelli, P. Chem. Rev., 2013, 113(8), 5924-5988.
[http://dx.doi.org/10.1021/cr4000732] [PMID: 23750879]
[16]
Halland, N.; Velgaard, T.; Jørgensen, K.A. J. Org. Chem., 2003, 68(13), 5067-5074.
[http://dx.doi.org/10.1021/jo0343026] [PMID: 12816459]
[17]
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]
[18]
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]
[19]
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]
[20]
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]
[21]
Gao, Y.; Ren, Q.; Wang, L. Wang. J. Chemistry, 2010, 16(44), 13068-13071.
[http://dx.doi.org/10.1002/chem.201002202] [PMID: 21031372]
[22]
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]
[23]
Calter, M.A. Wang. J. Org. Lett., 2009, 11(10), 2205-2208.
[http://dx.doi.org/10.1021/ol900586f] [PMID: 19366193]
[24]
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]
[25]
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]
[26]
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]
[27]
Ma, Z-W.; Wu, Y.; Sun, B.; Du, H-L.; Shi, W-M.; Tao, J-C. 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-W.; Liu, X-F.; Liu, J-T.; Liu, Z-J.; Tao, J-C. Tetrahedron Lett., 2017, 58(48), 4487-4490.
[http://dx.doi.org/10.1016/j.tetlet.2017.10.026]
[30]
Ma, Z-W.; Liu, Y-X.; Liu, J-T.; Tao, J-C. 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]
[32]
Song, X-X.; Liu, J.; Liu, M-M.; Wang, X.; Zhang, Z-F.; Wang, M-C.; Chang, J-B. Tetrahedron, 2014, 70(35), 5468-5474.
[http://dx.doi.org/10.1016/j.tet.2014.06.109]
[33]
Dajek, M.; Kowalczyk, R. Boratyński. P.J. Catal. Sci. Technol., 2018, 8(17), 4358-4363.
[http://dx.doi.org/10.1039/C8CY01199K]

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