Catalyst-Free, Multicomponent Reaction of Iodonium Ylides, Nitrosoarenes, and Olefins for the Synthesis of Isoxazolidine Derivatives

Yan-Rui Zhao; Lei Li; Jun Xuan

doi:10.1055/a-2107-5567

Synlett, Table of Contents

Synlett 2023; 34(17): 2022-2028
DOI: 10.1055/a-2107-5567

letter

Special Issue Thieme Chemistry Journals Awardees 2023

Catalyst-Free, Multicomponent Reaction of Iodonium Ylides, Nitrosoarenes, and Olefins for the Synthesis of Isoxazolidine Derivatives

Yan-Rui Zhao

^aAnhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, College of Chemistry & Chemical Engineering, Anhui University, Hefei, Anhui 230601, P. R. of China

,

Lei Li∗

^bShandong Key Laboratory of Optical Communication Science and Technology, School of Physics Science and Information Technology, Liaocheng University, Liaocheng 252000, P. R. of China

,

Jun Xuan∗

^aAnhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, College of Chemistry & Chemical Engineering, Anhui University, Hefei, Anhui 230601, P. R. of China

› Author Affiliations

Abstract

All articles of this category

Abstract

A general and efficient three-component protocol for the synthesis of isoxazolidines has been developed. A range of nitrosoarenes, olefins, as well as iodonium ylides can be subjected to this reaction to generate the N-aryl isoxazolidines derivatives with moderate to excellent yields. In addition, we demonstrate that this approach employs the 1,3-dipolar cycloaddition of nitrones generated in situ from iodonium ylides and nitroso compounds, with olefins in the absence of any catalysts and additives.

Key words

iodonium ylides - nitrosoarenes - olefins - N-aryl isoxazolidine derivatives - catalyst free

Full Text

References

References and Notes

1a Wessjohann LA, Rivera DG, Vercillo OE. Chem. Rev. 2009; 109: 796
1b Perreault S, Rovis T. Chem. Soc. Rev. 2009; 38: 3149
1c Volla CM. R, Atodiresei I, Rueping M. Chem. Rev. 2013; 114: 2390
1d Zhu J, Wang Q, Wang M. Eds. Multicomponent Reactions in Organic Synthesis . Wiley-VCH; Weinheim, Germany: 2014

2a Muller P. Acc. Chem. Res. 2004; 37: 243
2b Zhdankin VV. Eds. Hypervalent Iodine Chemistry: Preparation, Structure and Synthetic Applications of Polyvalent Iodine Compounds. John Wiley & Sons; Chichester, UK: 2013
2c Tong M.-H, Zhang X.-Y, Wang Y.-M, Wang Z.-K. Chin. J. Org. Chem. 2021; 41: 126
2d Xia M, Chao P, Feng W.-S, Cui X.-L. Org. Chem. Front. 2022; 9: 6999

3a Hackenberg J, Hanack M. J. Chem. Soc., Chem. Commun. 1991; 470
3b Yang R.-Y, Dai L.-X, Chen C.-G. J. Chem. Soc., Chem. Commun. 1992; 1487
3c Ochiai M, Okada T, Tada N, Yoshimura A. Org. Lett. 2008; 10: 1425
3d Vaitla J, Hopmann KH, Bayer A. Org. Lett. 2017; 19: 6688

4a Goudreau SR, Marcoux D, Charette AB. J. Org. Chem. 2009; 74: 470
4b Zhu C.-J, Yoshimura A, Ji L, Wei Y.-Y, Nemykin VN, Zhdankin VV. Org. Lett. 2012; 14: 3170
4c Deng C, Wang L.-J, Zhu J, Tang Y. Angew. Chem. Int. Ed. 2012; 51: 11620 ; Angew. Chem. 2012, 124, 11788
4d Guo J, Liu Y.-B, Li X.-Q, Liu X.-H, Lin L.-L, Feng X.-M. Chem. Sci. 2016; 7: 2717
4e Zhao Z.-G, Luo Y.-R, Liu S.-Y, Zhang L, Feng L, Wang Y. Angew. Chem. Int. Ed. 2018; 57: 3792 ; Angew. Chem. 2018, 130, 3854
4f Yang Z.-K, Liu J.-D, Li Y.-T, Ding J.-W, Zheng L.-Y, Liu Z.-Q. J. Org. Chem. 2022; 87: 14809

5a Matveeva ED, Podrugina TA, Taranova MA, Ivanova AM, Gleiter R, Zefirov NS. J. Org. Chem. 2012; 77: 5770
5b Matveeva ED, Podrugina TA, Taranova MA, Vinogradov DS, Gleiter R, Zefirov NS. J. Org. Chem. 2013; 78: 11691

6a Vaid R.-K, Hopkins T.-E. Tetrahedron Lett. 1997; 38: 6981
6b Batsila C, Gogonas EP, Kostakis G, Hadjiarapoglou LP. Org. Lett. 2003; 5: 1511
6c Müller P. Chem. Res. 2004; 37: 243

7 Hartmann M, Li Y, Mìck-Lichtenfeld C, Studer A. Chem. Eur. J. 2016; 22: 3485

8a Zhang L, Kong X.-J, Liu S.-Y, Zhao Z.-G, Yu Q, Wang W, Wang Y. Org. Lett. 2019; 21: 2923
8b Zhang L, Zhao Z.-G, Wang W, Liu S.-Y, Wang Y. Org. Lett. 2019; 21: 9171

9 Sen S, Barman D, Khan H, Das R, Maiti D. J. Org. Chem. 2022; 87: 12164

10a Zhao B.-X, Wang Y, Zhang D.-M, Jiang R.-W, Wang G.-C, Shi J.-M, Huang X.-J, Chen W.-M, Che C.-T, Ye W.-C. Org. Lett. 2011; 13: 3888
10b Rescifina A, Chiacchio U, Corsaro A, Piperno A, Romeo RR. Eur. J. Med. Chem. 2011; 46: 129
10c Ma N, Yao Y, Zhao B.-X, Wang Y, Ye W.-C, Jiang S. Chem. Commun. 2014; 50: 9284
10d Berthet M, Cheviet T, Dujardin G, Parrot I, Martinez J. Chem. Rev. 2016; 116: 15235

11a Gioia C, Fini F, Mazzanti A, Bernardi L, Ricci A. J. Am. Chem. Soc. 2009; 131: 9614
11b LaLonde RL, Wang Z.-J, Mba M, Lackner AD, Toste FD. Angew. Chem. Int. Ed. 2010; 49: 598
11c Partridge KM, Guzei IA, Yoon TP. Angew. Chem. Int. Ed. 2010; 49: 930
11d Romeo G, Chiacchio U, Corsaro A, Merino P. Chem. Rev. 2010; 110: 3337
11e Kobayashi Y, Taniguchi Y, Hayama N, Inokuma T, Takemoto YA. Angew. Chem. Int. Ed. 2013; 52: 11114
11f Morita N, Kono R, Fukui K, Miyazawa A, Masu H, Azumaya I, Ban S, Hashimoto Y, Okamoto I, Tamura O. J. Org. Chem. 2015; 80: 4797
11g Klier L, Tur F, Poulsen PH, Jørgensen KA. Chem. Soc. Rev. 2017; 46: 1080

12a Brandi A, Cicchi S, Cordero FM, Goti A. Chem. Rev. 2003; 103: 1213
12b Stanley LM, Sibi MP. Chem. Rev. 2008; 108: 2887
12c Gothelf KV, Jørgensen KA. Chem. Rev. 1998; 98: 863
12d Appukkuttan P, Mehta VP, Van der Eycken EV. Chem. Soc. Rev. 2010; 39: 1467
12e Wang X, Weigl C, Doyle MP. J. Am. Chem. Soc. 2011; 133: 9572
12f Yang X, Cheng F, Kou YD, Pang S, Shen YC, Huang YY, Shibata N. Angew. Chem. Int. Ed. 2017; 56: 1510

13a Xie J, Xue Q.-C, Jin H.-M, Li H.-M, Cheng Y.-X, Zhu C.-J. Chem. Sci. 2013; 4: 1281
13b Chatterjee I, Fröhlich R, Studer A. Angew. Chem. Int. Ed. 2011; 50: 11257
13c Chakrabarty S, Chatterjee I, Wibbeling B, Daniliuc CG, Studer A. Angew. Chem. Int. Ed. 2014; 53: 5964
13d Barber JS, Styduhar ED, Pham HV, McMahon TC, Houk KN, Garg NK. J. Am. Chem. Soc. 2016; 138: 2512
13e Yao T.-L, Ren B.-G, Wang B, Zhao Y.-N. Org. Lett. 2017; 19: 3135
13f Sugita S, Takeda N, Tohnai N, Miyata M, Miyata O, Ueda M. Angew. Chem. Int. Ed. 2017; 56: 2469
13g Ramakrishna I, Ramaraju P, Baidya M. Org. Lett. 2018; 20: 1023
13h Yang H, Wei G, Jiang Z.-Y. ACS Catal. 2019; 9: 9599

14a Chen H, Wang Z.-F, Zhang Y.-N, Huang Y. J. Org. Chem. 2013; 78: 3503
14b Sharma P, Jadhav PD, Skaria M, Liu R.-S. Org. Biomol. Chem. 2017; 15: 9389
14c Kawade RK, Liu R.-S. Angew. Chem. Int. Ed. 2017; 56: 2035

15 Zhai P.-G, Li W.-H, Lin J.-Y, Li X, Wei W.-L, Chen W.-W. J. Org. Chem. 2021; 86: 17710

16a Xu Z.-J, Zhu D, Zeng X, Wang F, Tan B, Hou Y.-X, Lv Y.-B, Zhong G.-F. Chem. Commun. 2010; 46: 2504
16b Reddy AR, Guo Z, Siu FM, Lok CN, Liu F, Yeung KC, Zhou C.-Y, Che C.-M. Org. Biomol. Chem. 2012; 10: 9165
16c Molander GA, Cavalcanti LN. Org. Lett. 2013; 15: 3166
16d Pagar VV, Liu R.-S. Angew. Chem. Int. Ed. 2015; 54: 4923
16e Wu M.-Y, He W.-W, Liu X.-Y, Tan B. Angew. Chem. Int. Ed. 2015; 54: 9409
16f Gupta E, Nair SR, Kant R, Mohanan K. J. Org. Chem. 2018; 83: 14811
16g Li X, Feng T, Li D.-J, Chang H.-L, Gao W.-C, Wei W.-L. J. Org. Chem. 2019; 84: 4402

17 Li X, Zhai P.-G, Fang Y.-S, Li W.-H, Chang H.-H, Gao W.-C. Org. Chem. Front. 2021; 8: 988
18 Li X, Zheng L.-J, Gong X.-L, Chang H.-H, Gao W.-C, Wei W.-L. J. Org. Chem. 2021; 86: 1096

19a Cai B.-G, Luo S.-S, Li L, Li L, Xuan J, Xiao W.-J. CCS Chem. 2020; 2: 2764
19b Cheng X, Cai B.-G, Mao H, Lu J, Li L, Wang K, Xuan J. Org. Lett. 2021; 23: 4109
19c Zhou S.-J, Cai B.-G, Hu C.-X, Cheng X, Li L, Xuan J. Chin. Chem. Lett. 2021; 32: 2577
19d Cai B.-G, Li Q, Empel C, Li L, Koenigs RM, Xuan J. ACS Catal. 2022; 12: 11129
19e Chen Z.-L, Chen J.-R, Xuan J. Chin. Chem. Lett. 2022; 33: 2763
19f Cai B.-G, Xu G.-Y, Xuan J. Chin. Chem. Lett. 2023; 16: 108335

20 Zhao Y.-R, Li L, Xu G.-Y, Xuan J. Adv. Synth. Catal. 2022; 364: 506

21a Tahtaoui C, Parrot I, Guillier P, Galzi JL, Hibert M, Ilien B. J. Med. Chem. 2004; 47: 4300
21b Li L, Zhang J. Org. Lett. 2011; 13: 5940
21c Aïssa C, Ho KY. T, Tetlow DJ, Pin-Nó M, Klotz F. Angew. Chem. Int. Ed. 2014; 53: 4209
21d Manel A, Berreur J, Leroux FR, Panossian A. Org. Chem. Front. 2021; 8: 5289
21e Tanaka S, Iwase S, Kanda S, Kato M, Kiriyama Y, Kitamura M. Synthesis 2021; 53: 3121
21f Lepore SD, Schacht AL, Wiley MR. Tetrahedron Lett. 2002; 43: 8777

22 General Procedure To a sealed tube equipped with a magnetic stir bar were added 1a′ (0.20 mmol, 2.0 equiv), 2a (0.10 mmol, 10.7 mg, 1.0 equiv), 3a (0.20 mmol, 20.8 mg, 2.0 equiv), and dry DCM (1.0 mL). Then, the temperature of metal sand bath was set to 50 ℃, and the closed reaction system was stirred for 18 h. The solvent was removed by vacuum, and the crude product was purified by flash chromatography on silica gel silica: 200–300; eluant: petroleum ether/ethyl acetate (10:1) to provide pure product 4 as a yellow solid in 99% yield (33.8 mg). Dimethyl 2-(4-Hexylphenyl)-5-phenylisoxazolidine-3,3-dicarboxylate (5) ¹H NMR (400 MHz, CDCl₃, 300 K): δ = 7.54 (d, J = 6.9 Hz, 2 H), 7.42–7.33 (m, 3 H), 7.29–7.26 (m, 3 H), 7.09–7.06 (m, 2 H), 5.32 (dd, J = 9.3, 6.4 Hz, 1 H), 3.73 (s, 3 H), 3.48 (s, 3 H), 3.25–3.11 (m, 2 H), 2.55 (d, J = 7.5 Hz, 2 H), 1.27 (q, J = 5.4, 4.3 Hz, 8 H), 0.86 (d, J = 6.9 Hz, 3 H) ppm. ¹³C NMR (100 MHz, CDCl₃, 300 K): δ = 169.0, 168.3, 144.7, 139.0, 137.5, 128.6, 128.2, 127.0, 118.7, 79.0, 78.8, 78.8, 53.0, 52.7, 47.6, 35.3, 31.7, 31.5, 28.8, 22.6, 14.1 ppm. HRMS (APCI): m/z [M + H]⁺ calcd for C₂₅H₃₂NO₅: 426.2280; found: 426.2290. Dimethyl 5-Phenyl-2-(pyridin-2-yl)isoxazolidine-3,3-dicarboxylate (17) ¹H NMR (400 MHz, CDCl₃, 300 K): δ = 8.18–8.15 (m, 1 H), 7.61–7.57 (m, 1 H), 7.45–7.33 (m, 5 H), 7.15 (d, J = 8.4 Hz, 1 H), 6.83–6.80 (m, 1 H), 5.34 (dd, J = 9.1, 6.4 Hz, 1 H), 3.79 (d, J = 8.2 Hz, 6 H), 3.37 (dd, J = 12.8, 6.4 Hz, 1 H), 3.05 (dd, J = 12.8, 9.2 Hz, 1 H) ppm. ¹³C NMR (100 MHz, CDCl₃, 300 K): δ = 169.4, 168.8, 158.5, 146.7, 137.8, 137.0, 128.7, 128.7, 126.8, 116.9, 109.9, 80.4, 75.4, 53.3, 53.2, 47.7 ppm. HRMS (APCI): m/z [M + H]⁺ calcd for C₁₈H₁₉N₂O₅: 343.1249; found: 343.1272. Dimethyl 5-Benzyl-2-phenylisoxazolidine-3,3-dicarboxylate (27) ¹H NMR (400 MHz, CDCl₃, 300 K): δ = 7.34–7.23 (m, 9 H), 7.01 (q, J = 4.4 Hz, 1 H), 4.60–4.53 (m, 1 H), 3.62 (s, 3 H), 3.55 (s, 3 H), 3.21 (dd, J = 13.8, 6.7 Hz, 1 H), 2.96–2.90 (m, 2 H), 2.81 (dd, J = 12.7, 8.7 Hz, 1 H) ppm. ¹³C NMR (100 MHz, CDCl₃, 300 K): δ = 168.8, 168.6, 147.1, 137.3, 129.2, 128.5, 128.3, 126.7, 123.7, 117.8, 78.4, 77.8, 52.9, 52.8, 45.4, 38.9 ppm. HRMS (APCI): m/z [M + H]⁺ calcd for C₂₀H₂₂NO₅: 356.1498; found: 356.1497. Dimethyl 5-(2-Oxopyrrolidin-1-yl)-2-phenylisoxazolidine-3,3-dicarboxylate (30) ¹H NMR (400 MHz, CDCl₃, 300 K): δ = 7.24 (d, J = 4.1 Hz, 4 H), 7.04–6.97 (m, 1 H), 4.45–4.38 (m, 1 H), 3.69 (s, 3 H), 3.51 (s, 3 H), 2.97 (dd, J = 12.5, 5.6 Hz, 1 H), 2.68 (dd, J = 12.3, 9.6 Hz, 1 H), 1.86–1.64 (m, 6 H), 1.53 (dd, J = 13.1, 8.0 Hz, 2 H), 1.28–1.17 (m, 3 H), 1.02–0.93 (m, 2 H) ppm. ¹³C NMR (100 MHz, CDCl₃, 300 K): δ = 169.2, 168.6, 147.3, 128.3, 123.4, 117.6, 78.4, 75.5, 52.9, 52.7, 46.5, 40.2, 35.3, 33.6, 33.2, 26.4, 26.2, 26.1 ppm. HRMS (APCI): m/z [M + H]⁺ calcd for C₂₀H₂₈NO₅: 362.1967; found: 362.1966. Dimethyl 5-Formyl-5-methyl-2-phenylisoxazolidine-3,3-dicarboxylate (37) ¹H NMR (400 MHz, CDCl₃, 300 K): δ = 9.68 (s, 1 H), 7.37 (d, J = 8.3 Hz, 2 H), 7.29 (d, J = 7.6 Hz, 2 H), 7.12 (t, J = 7.3 Hz, 1 H), 3.80 (s, 3 H), 3.32 (s, 3 H), 3.17 (d, J = 13.0 Hz, 1 H), 3.00 (d, J = 13.0 Hz, 1 H), 1.49 (s, 3 H) ppm. ¹³C NMR (100 MHz, CDCl₃, 300 K): δ = 203.1, 168.4, 167.0, 145.7, 128.3, 125.3, 119.6, 84.0, 77.9, 53.1, 52.5, 45.8, 17.4 ppm. HRMS (APCI): m/z [M + H]⁺ calcd for C₁₅H₁₈NO₆: 308.1134; found: 308.1135. Methyl 3-Acetyl-2,5-diphenylisoxazolidine-3-carboxylate (45) ¹H NMR (400 MHz, CDCl₃, 300 K): δ = 7.48–7.43 (m, 2 H), 7.42–7.34 (m, 3 H), 7.31–7.26 (m, 2 H), 7.20 (dd, J = 8.8, 1.1 Hz, 2 H), 7.05–7.00 (m, 1 H), 5.39 (dd, J = 8.9, 6.4 Hz, 1 H), 3.72 (s, 3 H), 3.41 (dd, J = 12.9, 6.4 Hz, 1 H), 2.86 (dd, J = 12.9, 9.0 Hz, 1 H), 2.15 (s, 3 H) ppm. ¹³C NMR (100 MHz, CDCl₃, 300 K): δ = 203.5, 168.8, 146.8, 137.3, 128.8, 128.7, 128.6, 126.5, 123.3, 116.7, 83.5, 79.1, 53.0, 46.5, 26.7 ppm. HRMS (APCI): m/z [M + H]⁺ calcd for C₁₉H₂₀NO₄: 326.1392; found: 326.1390. For the Synthesis of 11, 13, 39, and 40 To a sealed tube equipped with a magnetic stir bar were added 1a′ (0.20 mmol, 2.0 equiv), 2 (0.10 mmol, 1.0 equiv), 3 (0.20 mmol, 2.0 equiv), and dry DCM (1.0 mL). Then, the temperature of metal sand bath was set to 70 ℃, and the closed reaction system was stirred for 18 h. The solvent was removed by vacuum, and the crude product was purified by flash chromatography on silica gel silica: 200–300; eluant: petroleum ether/ethyl acetate (10:1) to provide pure product. Dimethyl 2-Phenyltetrahydrofuro[3,2-d]isoxazole-3,3(2H)-dicarboxylate (40) ¹H NMR (400 MHz, CDCl₃, 300 K): δ = 7.41 (s, 2 H), 7.28–7.24 (m, 3 H), 7.12 (t, J = 7.3 Hz, 1 H), 5.99 (d, J = 5.3 Hz, 1 H), 4.29–4.22 (m, 1 H), 4.03–3.99 (m, 1 H), 3.86 (dd, J = 6.4, 3.1 Hz, 1 H), 3.83 (s, 3 H), 3.32 (s, 3 H), 2.07 (s, 1 H), 1.92–1.83 (m, 1 H) ppm. ¹³C NMR (100 MHz, CDCl₃, 300 K): δ = 167.1, 166.2, 146.0, 128.1, 125.8, 121.1, 104.4, 82.7, 69.1, 54.2, 52.8, 52.1, 29.1 ppm. HRMS (APCI): m/z [M + H]⁺ calcd for C₁₅H₁₈NO₆: 308.1134; found: 308.1134.

Supplementary Material

Supporting Information