Direct Synthesis of Nitrones via Transition-Metal-Free Ring-Opening of N-Tosylaziridines with the Nitrogen Atom of Various (E)-Aldoximes and (E)-Ketoximes

Xing Li; Wenjing Yan; Rui Zhang; Honghong Chang; Wenchao Gao; Xiuping Tian; Wenlong Wei

doi:10.1055/s-0039-1690186

Synthesis, Inhaltsverzeichnis

Synthesis 2019; 51(21): 4043-4057
DOI: 10.1055/s-0039-1690186

paper

Direct Synthesis of Nitrones via Transition-Metal-Free Ring-Opening of N-Tosylaziridines with the Nitrogen Atom of Various (E)-Aldoximes and (E)-Ketoximes

Xing Li ∗

Department of Biomedical Engineering, Taiyuan University of Technology, 79 West Yingze Street, Taiyuan 030024, P. R. of China eMail: lixing@tyut.edu.cn eMail: txp1963@sina.com

,

Wenjing Yan

,

Rui Zhang

,

Honghong Chang

,

Wenchao Gao

,

Xiuping Tian∗

Department of Biomedical Engineering, Taiyuan University of Technology, 79 West Yingze Street, Taiyuan 030024, P. R. of China eMail: lixing@tyut.edu.cn eMail: txp1963@sina.com

,

Wenlong Wei

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

The KOH-, K₂CO₃-, or Et₃N-catalyzed ring-opening reaction of N-tosylaziridines using the nitrogen atom of a series of (E)-aldoximes and (E)-ketoximes as a nucleophilic atom instead of an oxygen atom was developed to construct various nitrones under mild reaction conditions. Diverse (E)-aldoximes and (E)-ketoximes were demonstrated to be compatible with this reaction and the products of O-ring-opening reactions were not detected for most examples.

Key words

nitrone - N-tosylaziridine - oxime - KOH - ring opening

Volltext

Referenzen

References and notes

For selected reviews, see:

1a Anderson LL. Asian J. Org. Chem. 2016; 5: 9
1b Shi W.-M, Ma X.-P, Su G.-F, Mo D.-L. Org. Chem. Front. 2016; 3: 116
1c Huple DB, Ghorpade S, Liu RS. Adv. Synth. Catal. 2016; 358: 1348
1d Yang J. Synlett 2012; 23: 2293

2a Hashimoto T, Maruoka K. Chem. Rev. 2015; 115: 5366
2b Stanley LM, Sibi MP. Chem. Rev. 2008; 108: 2887

For selected examples of [3 + 3] cycloadditions see:

2c Wang X, Xu X, Zavalij PY, Doyle MP. J. Am. Chem. Soc. 2011; 133: 16402
2d Qian Y, Xu X, Wang X, Zavalij PJ, Hu W, Doyle MP. Angew. Chem. Int. Ed. 2012; 51: 5900

For selected examples of [3 + 2] cycloadditions see:

2e Zheng L, Gao F, Yang C, Gao G.-L, Zhao Y, Gao Y, Xia W. Org. Lett. 2017; 19: 5086
2f Kumar SC. V, Ramana CV. Org. Lett. 2015; 17: 2870

For selected reviews on synthesis and transformations of nitrones, see:

3a Gothelf KV, Jørgensen KA. Chem. Rev. 1998; 98: 863
3b Bonin M, Chauveau A, Micouin L. Synlett 2006; 2349
3c Revuelta J, Cicchi S, Goti A, Brandi A. Synthesis 2007; 485
3d Pellissier H. Tetrahedron 2007; 63: 3235
3e Nair V, Suja TD. Tetrahedron 2007; 63: 12247
3f Murahashi S.-I, Imada Y. Chem. Rev. 2019; 119: 4684

4a Choudary BM, Bharathi B, Reddy CV, Kantam ML. Green Chem. 2002; 4: 279
4b Gella C, Ferrer E, Alibés R, Busque F, de March P, Figueredo M, Font J. J. Org. Chem. 2009; 74: 6365
4c Goti A, Nannelli L. Tetrahedron Lett. 1996; 37: 6025
4d Murahashi S, Mitsui H, Shiota T, Tsuda T, Watanabe S. J. Org. Chem. 1990; 55: 1736

5a Matassini C, Parmeggiani C, Cardona F, Goti A. Org. Lett. 2015; 17: 4082
5b Saladino R, Neri V, Cardona F, Goti A. Adv. Synth. Catal. 2004; 346: 639
5c Cicchi S, Goti A, Brandi A. J. Org. Chem. 1995; 60: 4743
5d Yudhas S, Kusuma I, Asao N. Tetrahedron 2015; 71: 6459

6a Soldaini G, Cardona F, Goti A. Org. Lett. 2007; 9: 473
6b Mirza-Aghayan M, Tavana MM, Boukherroub R. Tetrahedron Lett. 2014; 55: 5471
6c Christensen D, Joergensen KA. J. Org. Chem. 1989; 54: 126

7a Pfeiffer JY, Beauchemin AM. J. Org. Chem. 2009; 74: 8381
7b Maiuolo L, De Nino A, Merino P, Russo B, Stabile G, Nardi M, D’Agostino N, Bernardi T. Arab. J. Chem. 2016; 9: 25

8a Cisneros L, Serna P, Corma A. Angew. Chem. Int. Ed. 2014; 53: 9306
8b Denmark SE, Montgomery JI. J. Org. Chem. 2006; 71: 6211
8c Andrade MM, Barros MT, Pinto RC. Tetrahedron 2008; 64: 10521

9a Katahara S, Kobayashi S, Fujita K, Matsumoto T, Sato T, Chida N. J. Am. Chem. Soc. 2016; 138: 5246
9b Moran J, Pfeiffer JY, Gorelsky SI, Beauchemin AM. Org. Lett. 2009; 11: 1895
9c Nguyen TB, Martel A, Dhal R, Dujardin G. Org. Lett. 2008; 10: 4493
9d Li Z, Zhao J, Sun B, Zhou T, Liu M, Liu S, Zhang M, Zhang Q. J. Am. Chem. Soc. 2017; 139: 11702

Selected reviews:

10a Ha H.-J, Jung J.-H, Lee WK. Asian J. Org. Chem. 2014; 3: 1020
10b Pineschi M. Synlett 2014; 25: 1817
10c Stanković S, D’hooghe M, Catak S, Eum H, Waroquier M, Van Speybroeck V, De Kimpe N, Ha H.-J. Chem. Soc. Rev. 2012; 41: 643

Selected examples:

11a Arai K, Lucarini S, Salter MM, Ohta K, Yamashita Y, Kobayashi S. J. Am. Chem. Soc. 2007; 129: 8103
11b Chai Z, Yang P.-J, Zhang H, Wang S, Yang G. Angew. Chem. Int. Ed. 2017; 56: 650
11c Peruncheralathan S, Teller H, Schneider C. Angew. Chem. Int. Ed. 2009; 48: 4849

Selected examples:

12a Wu B, Gallucci JC, Parquette JR, RajanBabu TV. Angew. Chem. Int. Ed. 2009; 48: 1126
12b Fukuta Y, Mita T, Fukuda N, Kanai M, Shibasaki M. J. Am. Chem. Soc. 2006; 128: 6312
12c Schneider C. Angew. Chem. Int. Ed. 2009; 48: 2082
12d Chung BK. W, White CJ, Scully CC. G, Yudin AK. Chem. Sci. 2016; 7: 6662

13a Liew SK, Holownia A, Diaz DB, Cistrone PA, Dawson PE, Yudin AK. Chem. Commun. 2017; 53: 11237

For a review see:

13b Li J, Hu Y, Zhang D, Liu Q, Dong Y, Liu H. Adv. Synth. Catal. 2017; 359: 710

Selected examples:

14a Minakata S, Okumura S, Nagamachi T, Takeda Y. Org. Lett. 2011; 13: 2966
14b Yoshimura A, Nguyen KC, Klasen SC, Saito A, Nemykin VN, Zhdankin VV. Chem. Commun. 2015; 51: 7835
14c Yao T, Ren B, Wang B, Zhao Y. Org. Lett. 2017; 19: 3135

Selected examples:

15a Maimone TJ, Buchwald SL. J. Am. Chem. Soc. 2010; 132: 9990
15b Kontokosta D, Mueller DS, Wang H.-Y, Anderson LL. Org. Lett. 2013; 15: 4830
15c Ghosh R, Stridfeldt E, Olofsson B. Chem. Eur. J. 2014; 20: 8888

16a Jiao Y.-X, Ma X.-P, Su G.-F, Mo D.-L. Synthesis 2017; 49: 933
16b Wu S.-Y, Ma X.-P, Liang C, Mo D.-L. J. Org. Chem. 2017; 82: 3232
16c Chen C.-H, Liu Q.-Q, Ma X.-P, Feng Y, Liang C, Pan C.-X, Su G.-F, Mo D.-L. J. Org. Chem. 2017; 82: 6417
16d Mo X.-L, Chen C.-H, Liang C, Mo D.-L. Eur. J. Org. Chem. 2018; 150

17a Mo D.-L, Anderson LL. Angew. Chem. Int. Ed. 2013; 52: 6722
17b Mo D.-L, Wink DA, Anderson LL. Org. Lett. 2012; 14: 5180

18 Ma X.-P, Shi W.-M, Mo X.-L, Li X.-H, Li L.-G, Pan C.-X, Chen B, Su G.-F, Mo D.-L. J. Org. Chem. 2015; 80: 10098
19 Dondas HA, Cummins JE, Grigg R, Thornton-Pett M. Tetrahedron 2001; 57: 7951
20 Functional group R² bears larger steric hindrance than functional group R¹.

Zusatzmaterial

Supporting Information