Asymmetric Sequential Michael Addition and Cyclization Reactions of 2-(2-Nitrovinyl)phenols Catalyzed by Bifunctional Amino-Squaramides

Eva Veverková; Pavlína Molnosiová; Radovan Šebesta

doi:10.1055/s-0040-1719843

SynOpen, Table of Contents

CC BY-NC-ND 4.0 · SynOpen 2021; 05(04): 278-284
DOI: 10.1055/s-0040-1719843

paper

Asymmetric Sequential Michael Addition and Cyclization Reactions of 2-(2-Nitrovinyl)phenols Catalyzed by Bifunctional Amino-Squaramides

Eva Veverková

,

Pavlína Molnosiová

,

Radovan Šebesta ∗

Abstract

All articles of this category

Abstract

In this work, we describe the Michael addition–cyclization reaction of 2-(2-nitrovinyl)phenol with two different reactive Michael donors, which lead to chiral benzopyran derivatives. Specifically, bifunctional amino-squaramides with one or two chiral units in the side chains were evaluated as catalysts in these transformations. Furthermore, the utility of selected green solvents as reaction media for these processes was also tested. The best result was achieved with methyl-cyclopentanone-2-carboxylate as the Michael donor in ethyl (–)-l-lactate with quinine-based amino-squaramide as catalyst (yield 72%, dr >99:1, ee 99%).

Key words

asymmetric catalysis - organocatalysis - amino-squaramides - Michael cyclization reaction

Full Text

References

References
1 List B, Maruoka K. Asymmetric Organocatalysis, Workbench Edition. Thieme Chemistry; Stuttgart: 2012
2 Dalko PI. Comprehensive Enantioselective Organocatalysis: Catalysts, Reactions, and Applications. Wiley-VCH; Weinheim: 2013
3 Grondal C, Jeanty M, Enders D. Nat. Chem. 2010; 2: 167
4 Enders D, Grondal C, Huttl MR. M. Angew. Chem. Int. Ed. 2007; 46: 1570
5 Yu X, Wang W. Org. Biomol. Chem. 2008; 6: 2037
6 Pellissier H. Adv. Synth. Catal. 2012; 354: 237
7 Vetica F, de Figueiredo RM, Orsini M, Tofani D, Gasperi T. Synthesis 2015; 47: 2139
8 Tanmoy C, Zhao JC.-G. Adv. Synth. Catal. 2018; 360: 2
9 Reddy Gajulapalli VP, Vinayagam P, Kesavan V. RSC Adv. 2015; 5: 7370
10 Sun P, Meng C.-Y, Zhou F, Li X.-S, Xie J.-W. Tetrahedron 2014; 70: 9330
11 Narayanaperumal S, Rivera DG, Silva RC, Paixão MW. ChemCatChem 2013; 5: 2756
12 Hoashi Y, Yabuta T, Takemoto Y. Tetrahedron Lett. 2004; 45: 9185
13 Hoashi Y, Yabuta T, Yuan P, Miyabe H, Takemoto Y. Tetrahedron 2006; 62: 365
14 Dai Q, Arman H, Zhao JC.-G. Chem. Eur. J. 2013; 19: 1666
15 Cho B, Tan C.-H, Wong MW. Org. Biomol. Chem. 2011; 9: 4550
16 He P, Liu X, Shi J, Lin L, Feng X. Org. Lett. 2011; 13: 936
17 Li C, Shu X, Li L, Zhang G, Jin R, Cheng T, Liu G. Chem. Asian J. 2016; 11: 2072
18 Zhou Y, Liu X.-W, Gu Q, You S.-L. Synlett 2016; 27: 586
19 Sun H.-R, Zhao Q, Yang H, Yang S, Gou B.-B, Chen J, Zhou L. Org. Lett. 2019; 21: 7143
20 Ramachary DB, Madhavachary R, Prasad MS. Org. Biomol. Chem. 2012; 10: 5825
21 Enders D, Urbanietz G, Hahn R, Raabe G. Synthesis 2012; 44: 773
22 Ramachary DB, Sakthidevi R, Shruthi KS. Chem. Eur. J. 2012; 18: 8008
23 Ramachary DB, Shruthi KS. Org. Biomol. Chem. 2014; 12: 4300
24 Andrés JM, Losada J, Maestro A, Rodríguez-Ferrer P, Pedrosa R. J. Org. Chem. 2017; 82: 8444
25 Storer RI, Aciro C, Jones LH. Chem. Soc. Rev. 2011; 40: 2330
26 Alemán J, Parra A, Jiang H, Jørgensen KA. Chem. Eur. J. 2011; 17: 6890
27 Zhao B.-L, Li J.-H, Du D.-M. Chem. Rec. 2017; 17: 994
28 Karahan S, Tanyeli C. Tetrahedron Lett. 2018; 59: 3725
29 Chauhan P, Mahajan S, Kaya U, Hack D, Enders D. Adv. Synth. Catal. 2015; 357: 253
30 Roy TK, Parhi B, Ghorai P. Angew. Chem. Int. Ed. 2018; 57: 9397
31 Xiao Y, Jiang R, Wang Y, Zhou Z. Adv. Synth. Catal. 2018; 360: 1961
32 Zhou Y, Wei Y.-L, Rodriguez J, Coquerel Y. Angew. Chem. Int. Ed. 2019; 58: 456
33 Chaudhari PD, Hong B.-C, Wen C.-L, Lee G.-H. ACS Omega 2019; 4: 655
34 Tang Q.-G, Cai S.-L, Wang C.-C, Lin G.-Q, Sun X.-W. Org. Lett. 2020; 22: 3351
35 Mo Y, Zhang X, Yao Y, Duan C, Ye L, Shi Z, Zhao Z, Li X. J. Org. Chem. 2021; 86: 4448
36 Ni Q, Wang X, Zeng D, Wu Q, Song X. Org. Lett. 2021; 23: 2273
37 Modrocká V, Veverková E, Mečiarová M, Šebesta R. J. Org. Chem. 2018; 83: 13111
38 Modrocká V, Veverková E, Baran R, Šebesta R. Chemistry Select 2018; 3: 1466
39 Peňaška T, Palchykov V, Rakovský E, Addová G, Šebesta R. Eur. J. Org. Chem. 2021; 1693
40 Clarke CJ, Tu W.-C, Levers O, Bröhl A, Hallett JP. Chem. Rev. 2018; 118: 747
41 Pace V, Hoyos P, Castoldi L, Domínguez de María P, Alcántara AR. ChemSusChem 2012; 5: 1369
42 Pereira CS. M, Silva VM. T. M, Rodrigues AE. Green Chem. 2011; 13: 2658
43 Tang S, Zhao H. RSC Adv. 2014; 4: 11251
44 Liu Y, Lu A, Hu K, Wang Y, Song H, Zhou Z, Tang C. Eur. J. Org. Chem. 2013; 4836
45 Albrecht Ł, Dickmeiss G, Acosta FC, Rodríguez-Escrich C, Davis RL, Jørgensen KA. J. Am. Chem. Soc. 2012; 134: 2543
46 Malerich JP, Hagihara K, Rawal VH. J. Am. Chem. Soc. 2008; 130: 14416
47 Baran R, Veverková E, Škvorcová A, Šebesta R. Org. Biomol. Chem. 2013; 11: 7705
48 Tsakos M, Kokotos CG, Kokotos G. Adv. Synth. Catal. 2012; 354: 740
49 Tena Pérez V, Fuentes de Arriba ÁL, Monleón LM, Simón L, Rubio OH, Sanz F, Morán JR. Eur. J. Org. Chem. 2014; 3242

Supplementary Material

Supporting Information