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Letters in Organic Chemistry

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

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Research Article

Squaramide-Catalyzed Enantioselective Michael Addition of Pyrazol-3- ones to ortho-Quinone Methides

Author(s): Laura Carceller-Ferrer, Gonzalo Blay*, José R. Pedro* and Carlos Vila

Volume 17, Issue 11, 2020

Page: [837 - 844] Pages: 8

DOI: 10.2174/1876402911666190806105543

Price: $65

Abstract

A bifunctional squaramide catalyzed the enantioselective Michael addition of pyrazol-3- ones to ortho-quinone methides, generated in situ from 2-(1-tosylalkyl)phenols is presented. The corresponding chiral pyrazolones are obtained with good to excellent yields (27-98%) and enantiomeric excess (14-99% ee).

Keywords: Asymmetric catalysis, organocatalysis, ortho-quinone methides, pyrazolones, Michael reaction.

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[1]
(a) Bruins, J.J.; Albada, B.; van Delft, F. Chemistry, 2018, 24(19), 4749-4756.
[http://dx.doi.org/10.1002/chem.201703919] [PMID: 29068513]
(b) Caruana, L.; Fochi, M.; Bernardi, L. Molecules, 2015, 20(7), 11733-11764.
[http://dx.doi.org/10.3390/molecules200711733] [PMID: 26121398]
(c) Pathak, T.P.; Sigman, M.S. J. Org. Chem., 2011, 76(22), 9210-9215.
[http://dx.doi.org/10.1021/jo201789k] [PMID: 21999240]
(d) Bai, W-J.; David, J.G.; Feng, Z-G.; Weaver, M.G.; Wu, K-L.; Pettus, T.R.R. Acc. Chem. Res. 2014, 47(12), 3655-3664.
[http://dx.doi.org/10.1021/ar500330x] [PMID: 25469551 ]
(e) Singh, M.S.; Nagaraju, A.; Anad, N.; Chowdhury, S. RSC Advances, 2014, 4, 55924-55959.
[http://dx.doi.org/10.1039/C4RA11444B]
f Willis, N.J.; Bray, C.D. Chemistry, 2012, 18(30), 9160-9173.
[http://dx.doi.org/10.1002/chem.201200619] [PMID: 22707392 ]
(g) Wang, Z; Sun, J.; Synthesis, 2015, 47, 3629-3644.
[http://dx.doi.org/10.1055/s-0035-1560356]
(h) Osipov, D.V.; Osyanin, V.A.; Klimochkin, Y.N. Russ. Chem. Rev 2017, 86, 625-687.
[http://dx.doi.org/10.1070/RCR4679]
(i) Jaworski, A.A; Scheidt, K.A. J Org. Chem 2016, 81(21), 10145-10153.
[http://dx.doi.org/10.1021/acs.joc.6b01367] [PMID: 27513764]
[2]
(a) Yanga, B.; Gao, S. Chem. Soc. Rev., 2018, 47, 7926-7953.
[http://dx.doi.org/10.1039/C8CS00274F] [PMID: 29993045 ]
(b) Spanka, M.; Schneider, C. Org. Lett., 2018, 20(16), 4769-4772.
[http://dx.doi.org/10.1021/acs.orglett.8b01865] [PMID: 30074397]
[3]
(a) Song, L.; Huang, F.; Guo, L.; Ouyang, M-A.; Tong, R. Chem. Commun. (Camb.) 2017, 53(44), 6021-6024.
[http://dx.doi.org/10.1039/C7CC03037A] [PMID: 28524196 ]
(b) Zeng, B-S.; Yu, X.; Siu, P.W.; Scheidt, K.A. Chem. Sci. (Camb.), 2014, 5, 2277-2281.
[http://dx.doi.org/10.1039/c4sc00423j]
(c) Carbone, A.; Lucas, C.L.; Moody, C.J. J. Org. Chem., 2012, 77(20), 9179-9189.
[http://dx.doi.org/10.1021/jo301738u] [PMID: 23020609 ]
(d) George, J.H.; Hesse, M.D.; Baldwin, J.E.; Adlington, R.M. Org. Lett., 2010, 12(15), 3532-3535.
[http://dx.doi.org/10.1021/ol101380a] [PMID: 20590087]
(e) Malerich, J.P.; Maimone, T.J.; Elliott, G.I.; Trauner, D. J. Am. Chem. Soc., 2005, 127(17), 6276-6283.
[http://dx.doi.org/10.1021/ja050092y] [PMID: 15853334]
[4]
(a) Miao, M.; Yin, W.; Wang, L. J. Org. Chem., 2018, 83, 10602-10612.
[http://dx.doi.org/10.1021/acs.joc.8b01428] [PMID: 30067907]
(b) Basha, R.S.; Chen, C-W.; Reddy, D.M.; Lee, C-F. Chem. Asian J., 2018, 13(17), 2475-2483.
[http://dx.doi.org/10.1002/asia.201800233] [PMID: 29624908]
(c) Liang, W.; Yin, W.; Wang, T.; Qiu, F.G.; Zhao, J. Tetrahedron Lett 2018, 59, 1742-1747.
[http://dx.doi.org/10.1016/j.tetlet.2018.03.069]
(d) Huang, H.; Kang, J.Y. Org. Lett. 2017, 19(21), 5988-5991.
[http://dx.doi.org/10.1021/acs.orglett.7b03019] [PMID: 29064709 ]
(e) Lewis, R.S.; Garza, C.J.; Dang, A.T.; Pedro, T.K.A.; Chain, W.J. Org. Lett., 2015, 17(9), 2278-2281.
[http://dx.doi.org/10.1021/acs.orglett.5b00972] [PMID: 25906358 ]
(f) Wua, B.; Gao, X.; Yan, Z.; Huang, W-X.; Zhou, Y-G. Tetrahedron Lett., 2015, 56, 4334-4338.
[http://dx.doi.org/10.1016/j.tetlet.2015.05.076]
[5]
Varvounis, G. Pyrazol-3-ones. Part IV: Synthesis and Applications. Advances in Heterocyclic Chemistry, (Ed.: A. R. Katritzky); Academic Press: New York, , 2009; 98, pp. 143-224.
[6]
Horton, D.A.; Bourne, G.T.; Smythe, M.L. Chem. Rev., 2003, 103(3), 893-930.
[http://dx.doi.org/10.1021/cr020033s] [PMID: 12630855]
[7]
Yuan, W.J.; Yasuhara, T.; Shingo, T.; Muraoka, K.; Agari, T.; Kameda, M.; Uozumi, T.; Tajiri, N.; Morimoto, T.; Jing, M.; Baba, T.; Wang, F.; Leung, H.; Matsui, T.; Miyoshi, Y.; Date, I. BMC Neurosci., 2008, 9, 75.
[http://dx.doi.org/10.1186/1471-2202-9-75] [PMID: 18671880]
[8]
Dipyrone.Brayfield, A., Ed.; Martindale: The Complete Drug Reference; Pharmaceutical Press 2014.
[9]
Fujimori, Y.; Katsuno, K.; Nakashima, I.; Ishikawa-Takemura, Y.; Fujikura, H.; Isaji, M. J. Pharmacol. Exp. Ther., 2008, 327(1), 268-276.
[http://dx.doi.org/10.1124/jpet.108.140210] [PMID: 18583547]
[10]
(a) Chauhan, P.; Mahajan, S.; Enders, D. Chem. Commun. (Camb.) 2015, 51(65), 12890-12907.
[http://dx.doi.org/10.1039/C5CC04930J] [PMID: 26178319 ]
(b) Liu, S.; Bao, X.; Wang, B. Chem. Commun. (Camb.), 2018, 54(82), 11515-11529.
[http://dx.doi.org/10.1039/C8CC06196C] [PMID: 30225504]
[11]
(a) Vila, C.; Rendón-Patiño, A.; Montesinos-Magraner, M.; Blay, G.; Muñoz, M.C.; Pedro, J.R. Adv. Synth. Catal 2018, 360, 859-864.
[http://dx.doi.org/10.1002/adsc.201701217]
(b) Vila, C.; Rostoll-Berenguer, J.; Sánchez-García, R.; Blay, G.; Fernández, I.; Muñoz, M.C.; Pedro, J.R. J. Org. Chem., 2018, 83(12), 6397-6407.
[http://dx.doi.org/10.1021/acs.joc.8b00612] [PMID: 29856221]
(c) Montesinos-Magraner, M.; Vila, C.; Rendón-Patiño, A.; Blay, G.; Fernández, I.; Muñoz, M.C.; Pedro, J.R. ACS Catal. 2016, 6, 2689-2693.
[http://dx.doi.org/10.1021/acscatal.6b00260]
(d) Blay, G.; Fernández, I.; Pedro, J.R.; Vila, C. Synthesis 2012, 44, 3590-3594.
[http://dx.doi.org/10.1055/s-0032-1317161]
(e) Blay, G.; Fernández, I.; Muñoz, M.C.; Pedro, J.R.; Recuenco, A.; Vila, C. J. Org. Chem., 2011, 76(15), 6286-6294.
[http://dx.doi.org/10.1021/jo2010704] [PMID: 21682323]
(f) Blay, G.; Fernández, I.; Monleón, A.; Pedro, J.R.; Vila, C. Org. Lett., 2009, 11(2), 441-444.
[http://dx.doi.org/10.1021/ol802509m] [PMID: 19128193]
[12]
(a) Vila, C.; Amr, F.I.; Blay, G.; Muñoz, M.C.; Pedro, J.R. Chem. Asian J. 2016, 11(10), 1532-1536.
[http://dx.doi.org/10.1002/asia.201600325] [PMID: 27038062 ]
(b) Amr, F.I.; Vila, C.; Blay, G.; Muñoz, M.C.; Pedro, J.R. Adv. Synth. Catal., 2016, 358, 1583-1588.
[http://dx.doi.org/10.1002/adsc.201600036]
[13]
Zhou, J.; Huang, W-J.; Jiang, G-F. Org. Lett., 2018, 20(4), 1158-1161.
[http://dx.doi.org/10.1021/acs.orglett.8b00025] [PMID: 29420039]
[14]
(a) Weinert, E.E.; Dondi, R.; Colloredo-Melz, S.; Frankenfield, K.N.; Mitchell, C.H. J. Am. Chem. Soc. 2006, 128, 11940-11947.
[http://dx.doi.org/10.1021/ja062948k] [PMID: 16953635 ]
(b) Caruana, L.; Mondatori, M.; Corti, V.; Morales, S.; Mazzanti, A.; Fochi, M.; Bernardi, L. Chemistry, 2015, 21(16), 6037-6041.
[http://dx.doi.org/10.1002/chem.201500710] [PMID: 25766504]
[15]
(a) Tian, S-K.; Chen, Y.; Hang, J.; Tang, L.; McDaid, P.; Deng, L. Acc. Chem. Res 2004, 37(8), 621-631.
[http://dx.doi.org/10.1021/ar030048s] [PMID: 15311961 ]
(b) Marcelli, T.; Hiemstra, H. Synthesis 2010, 1229-1279.
[http://dx.doi.org/10.1055/s-0029-1218699]
(c) Connon, S. J. Chem., 2006, 12(21), 5418-5427.
[http://dx.doi.org/10.1002/chem.200501076] [PMID: 16514689]
(d) Alemán, J.; Parra, A.; Jiang, H.; Jørgensen, K.A. Chemistry, 2011, 17(25), 6890-6899.
[http://dx.doi.org/10.1002/chem.201003694] [PMID: 21590822]
(e) Doyle, A.G.; Jacobsen, E.N. Chem. Rev., 2007, 107(12), 5713-5743.
[http://dx.doi.org/10.1021/cr068373r] [PMID: 18072808]
[16]
Guo, W.; Wu, B.; Zhou, X.; Chen, P.; Wang, X.; Zhou, Y-G.; Liu, Y.; Li, C. Angew. Chem. Int. Ed., 2015, 54, 4522-4526.
[http://dx.doi.org/10.1002/anie.201409894]
[17]
Palmieri, A.; Petrini, M.; Shaikh, R.R. Org. Biomol. Chem., 2010, 8(6), 1259-1270.
[http://dx.doi.org/10.1039/B919891A] [PMID: 20204191]
[18]
(a) Marianacci, O.; Micheletti, G. Chemistry, 2007, 13, 8338-8351.
[http://dx.doi.org/10.1002/chem.200700908] [PMID: 17705329 ]
(b) Petrini, M Chem. Rev., 2005, 105(11), 3949-3977.
[http://dx.doi.org/10.1021/cr050528s] [PMID: 16277367 ]
(c) Yin, B.; Zhang, Y.; Xu, L-W. Synthesis, 2010, 21, 3583-3595.
[http://dx.doi.org/10.1055/s-0030-1258241]

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