An Efficient Method for Opening N-Tosylaziridines with Silylated Nucleo­philes by Using Polystyrene-Supported 1,5,7-Triazabicyclo[4.4.0]dec-5-ene as a Reusable Organocatalyst

Abstract

Polystyrene-supported 1,5,7-triazabicyclo[4.4.0]dec-5-ene (PS-TBD) catalyzes the ring opening of N-tosylaziridines with trimethylsilyl cyanide, trimethylsilyl azide, or trimethylsilyl halides to give the corresponding products in high yields. PS-TBD can be easily recovered and reused without significant loss of catalytic activity.

Keywords

catalysis - polymers - ring opening - heterocycles - aziridines - sulfonamides

• References

• 1a Sweeny JB. Chem. Soc. Rev. 2002; 31: 247
• 1b Pearson WH, Lian BN, Bergmeier SC In Comprehensive Heterocyclic Chemistry II . Vol. 1a. Katritzky AR, Rees CW, Scriven EF. V. Pergamon; Oxford: 1996. Chap. 1.01, 1
• 1c Tanner D. Angew. Chem., Int. Ed. Engl. 1994; 33: 599
• 1d Padwa A, Woolhouse AD In Comprehensive Heterocyclic Chemistry . Vol. 7. Katritzky AR, Rees CW. Pergamon; Oxford: 1984. Chap. 5.04, 47

For recent reviews, see:
• 2a Hu XE. Tetrahedron 2004; 60: 2701
• 2b Watson ID. G, Yu L, Yudin AK. Acc. Chem. Res. 2006; 39: 194
• 2c Aziridines and Epoxides in Organic Synthesis . Yudin AK. Wiley-VCH; Weinheim: 2006
• 2d Singh GS, D’hooghe M, De Kimpe N. Chem. Rev. 2007; 107: 2080
• 2e Lu P. Tetrahedron 2010; 66: 2549
• 3a Matsubara S, Kodama T, Utimoto K. Tetrahedron Lett. 1990; 31: 6379
• 3b Osborn HM. I, Sweeney JB, Howson B. Synlett 1994; 145
• 3c Leung WH, Yu MT, Wu MC, Yeung LL. Tetrahedron Lett. 1996; 37: 891
• 3d Ferraris D, Drury III WJ, Cox C, Lectka J. J. Org. Chem. 1998; 63: 4568
• 3e Li Z, Fernández M, Jacobsen EN. Org. Lett. 1999; 1: 1611
• 3f Chandrasekhar M, Sekar G, Singh VK. Tetrahedron Lett. 2000; 41: 4677
• 3g Shin S.-H, Han EY, Park CS, Lee WK, Ha H.-J. Tetrahedron: Asymmetry 2000; 11: 3293
• 3h Reddy MA, Reddy LR, Bhanumathi N, Rao KR. Chem. Lett. 2001; 246
• 3i Chandrasekhar M, Sekar G, Singh VK. Tetrahedron Lett. 2000; 41: 10079
• 3j Yadav JS, Reddy BV. S, Kumar GM, Murhty VS. R. Synth. Commun. 2002; 32: 1797
• 3k Mita T, Fujimori I, Wada R, Wen J, Kanai M, Shibasaki M. J. Am. Chem. Soc. 2005; 127: 11252
• 3l Fukuta Y, Mita T, Fukuda N, Kanai M, Shibasaki M. J. Am. Chem. Soc. 2006; 128: 6312
• 3m Fujimori I, Mita T, Maki K, Shiro M, Sato A, Furusho S, Kanai M, Shibasaki M. J. Am. Chem. Soc. 2006; 128: 16438
• 3n Rowland EB, Rowland GB, Rivera-Otero E, Antilla JC. J. Am. Chem. Soc. 2007; 129: 12084
• 3o Yu R, Yamashita Y, Kobayashi S. Adv. Synth. Catal. 2009; 351: 157
• 3p Wu B, Gallucci JC, Parquette JR, RajanBabu TV. Angew. Chem. Int. Ed. 2009; 48: 1126
• 3q Hayashi Y, Kumamoto T, Kawahata M, Yamaguchi K, Ishikawa T. Tetrahedron 2010; 66: 3836
• 3r Bera M, Pratihar S, Roy S. J. Org. Chem. 2011; 76: 1475
• 4 Wu J, Hou X.-L, Dai L.-X. J. Org. Chem. 2000; 65: 1344
• 5a Minakata S, Okada Y, Oderaotoshi Y, Komatsu M. Org. Lett. 2005; 7: 3509
• 5b Wu J, Sun X, Xia H.-G. Eur. J. Org. Chem. 2005; 4769
• 5c Wu J, Sun X, Sun W. Org. Biomol. Chem. 2006; 4: 4231
• 5d Matsukawa S, Tsukamoto K. Org. Biomol. Chem. 2009; 6: 3792
• 5e Matsukawa S, Takahasi H, Harada T. Synth. Commun. 2013; 43: 406
• 6 Wu J, Sun X, Shengqing Y, Sun W. Tetrahedron Lett. 2006; 47: 4813

For recent reviews, see:
• 7a McNamara CA, Dixon MJ, Bradley M. Chem. Rev. 2002; 102: 3275
• 7b Benaglia M, Puglisi A, Cozzi F. Chem. Rev. 2003; 103: 3401
• 7c Cozzi F. Adv. Synth. Catal. 2006; 348: 1367
• 7d Sommer WJ, Weck M. Coord. Chem. Rev. 2007; 251: 860
• 7e Kwong CK, Huang R, Zhang M, Toy PH. Chem. Eur. J. 2007; 13: 2369
• 7f Buchmeiser MR. Chem. Rev. 2009; 109: 303
• 7g Wang Z, Chen G, Ding K. Chem. Rev. 2009; 109: 322
• 7h Ikegami S, Hamamoto H. Chem. Rev. 2009; 109: 583
• 7i Lu J, Toy PH. Chem. Rev. 2009; 109: 815
• 7j Kristensen TE, Hansen T. Eur. J. Org. Chem. 2010; 3179
• 8a Tomoi M, Kato Y, Kakiuchi H. Makromol. Chem. 1984; 185: 2117
• 8b Iijima K, Fukuda W, Tomoi M. J. Macromol. Sci., Part A: Pure Appl. Chem. 1992; 29: 249
• 8c Tamura Y, Fukuda W, Tomoi M. Synth. Commun. 1994; 24: 2907
• 8d Xu X, Mohan R, Morrissey MM. Tetrahedron Lett. 1997; 38: 7337
• 8e Boisnard S, Chastanet J, Zhu J. Tetrahedron Lett. 1999; 40: 7469
• 9a Simoni D, Rondanin R, Morini M, Baruchello R, Invidiata FP. Tetrahedron Lett. 2000; 41: 1607
• 9b For PS-TBD as a ligand in Cu-catalyzed 1,3-dipolar cycloaddition reactions, see: Coelho C, Diz P, Caamaño O, Sotelo E. Adv. Synth. Catal. 2010; 352: 1179
• 10a Fringuelli F, Pizzo F, Vittoriani C, Vaccaro L. Chem. Commun. 2004; 2756
• 10b Fringuelli F, Pizzo F, Vittoriani C, Vaccaro L. Eur. J. Org. Chem. 2006; 1231
• 10c Lanari D, Balini R, Palmieri A, Pizzo F, Vaccaro L. Eur. J. Org. Chem. 2011; 2874
• 11 Matsukawa S, Fujikawa S. Tetrahedron Lett. 2012; 53: 1075
• 12 Matsukawa S, Harada T, Yasuda S. Org. Biomol. Chem. 2012; 10: 4886
• 13 Thakur VV, Sudalai A. Tetrahedron Lett. 2003; 44: 989