ARTICLE

Direct Amination of N-Acyliminium Ion Surrogates: A Convenient Access to gem-Diamines Derivatives

  • Yang Jinming ,
  • Chu Xueqiang ,
  • Ji Shunjun
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  • a. Key Laboratory of Coastal Wetland Bioresources and Environmental Protection of Jiangsu Province, College of Chemistry and Chemical Engineering, Yancheng Teachers University, Yancheng 224002;
    b. Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, 215123

Received date: 2014-10-11

  Revised date: 2014-10-22

  Online published: 2014-10-23

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21172162, 21372174) and the Project Funded by the Priority Academic Program Development (PAPD) of Jiangsu Higher Education Institutions.

Abstract

A novel 4-methylbenzenesulfonic acid (PTSA)-catalyzed intermolecular amination of N-acyliminium species with various N-sources via benzylic C(sp3)-O activation of functionalized 2-oxo-1-pyrrolidine derivatives has been developed. This method provides an efficient and chromatography-free access to gem-diamines equivalent with moderate to good yields. Because of the importance of gem-diamine derivatives, the methodology is expected to have a significant value for practical applications.

Cite this article

Yang Jinming , Chu Xueqiang , Ji Shunjun . Direct Amination of N-Acyliminium Ion Surrogates: A Convenient Access to gem-Diamines Derivatives[J]. Chinese Journal of Organic Chemistry, 2014 , 34(12) : 2462 -2470 . DOI: 10.6023/cjoc201410017

References

[1] (a) Ricci, A. Modern Amination Reactions, Wiley-VCH, Weinheim, 2000. (b) Gobert, A.; Cara, B. D.; Cistarelli, L.; Millan, M. J. J. Pharmacol. Exp. Ther. 2003, 305, 338. (c) Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921. (d) Lawrence, S. A. Amines: Synthesis Properties, and Applications, Cambridge University Press, Cambridge, UK, 2004. (e) Müller, T. E.; Hultzsch, K. C.; Yus, M.; Foubelo, F.; Tada, M. Chem. Rev. 2008, 108, 3795. (f) Lu, T.; Lu, Z.; Ma, Z.-X.; Zhang, Y.; Hsung, R. P. Chem. Rev. 2013, 113, 4862.
[2] (a) Trost, B. M. Science 1991, 254, 1471. (b) Salvatore, R. N.; Yoon, C. H.; Jung, K. W. Tetrahedron 2001, 57, 7785. (c) Buchwald, S. L.; Mauger, C.; Mignani, G.; Scholz, U. Adv. Synth. Catal. 2006, 348. (d) Wuts, P. G. M.; Greene, T. W. Protective Groups in Organic Synthesis, 4th ed., Wiley-Interscience, New York, 2007. (e) Suzuki, K.; Hori, Y.; Kobayashi, T. Adv. Synth. Catal. 2008, 350, 652. (f) Long, T. R.; Maity, P. K.; Samarakoon, T. B.; Hanson, P. R. Org. Lett. 2010, 12, 2904.
[3] For selected reviews and examples see: (a) Hamid, M. H. S. A.; Slatford, P. A.; Williams, J. M. J. Adv. Synth. Catal. 2007, 349, 1555. (b) Guillena, G.; Ramon, D.; Yus, M. Chem. Rev. 2010, 110, 1611. (c) Rauws, T. R. M.; Maes, B. U. W. Chem. Soc. Rev. 2012, 41, 2463. (d) Shi, F.; Tse, M. K.; Zhou, S.; Pohl, M.-M.; Radnik, J.; Huebner, S.; Jaehnisch, K.; Brueckner, A.; Beller, M. J. Am. Chem. Soc. 2009, 131, 1775. (e) Bahn, S.; Imm, S.; Mevius, K.; Neubert, L.; Tillack, A.; Williams, J. M. J.; Beller, M. Chem.-Eur. J. 2010, 16, 3590.
[4] (a) Dobereiner, G. E.; Crabtree, R. H. Chem. Rev. 2010, 110, 681. (b) Suzuki, T. Chem. Rev. 2011, 111, 1825. (c) Hamid, M. H. S. A.; Allen, C. L.; Lamb, G. W.; Maxwell, A. C.; Maytum, H. C.; Watson, A. J. A.; Williams, J. M. J. J. Am. Chem. Soc. 2009, 131, 1766. (d) Shi, F.; Tse, M. K.; Cui, X.; Gordes, D.; Michalik, D.; Thurow, K.; Deng, Y.; Beller, M. Angew. Chem., Int. Ed. 2009, 48, 5912. (e) Michlik, S.; Kempe, R. Chem.-Eur. J. 2010, 16, 13193. (f) Watson, A. J. A.; Maxwell, A. C.; Williams, J. M. J. J. Org. Chem. 2011, 76, 2328. (g) Yu, X. C.; Liu, C. Z.; Jiang, L.; Xu, Q. Org. Lett. 2011, 13, 6184. (h) Zhang, E. L.; Tian, H. W.; Xu, S. D.; Yu, X. C.; Xu, Q. Org. Lett. 2013, 15, 2704. (i) Bala, M.; Verma, P. K.; Sharma, U.; Kumar, N.; Singh, B. Green Chem. 2013, 15, 1687.
[5] (a) Terrasson, V.; Marque, S.; Georgy, M.; Campagne, J.-M.; Prima, D. Adv. Synth. Catal. 2006, 348, 2063. (b) Motokura, K.; Nakagiri, N.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J. Org. Chem. 2007, 72, 6006. (c) Wang, G.-W.; Shen, Y.-B.; Wu, X.-L. Eur. J. Org. Chem. 2008, 4367. (d) Reddy, C. R.; Jithender, E. Tetrahedron Lett. 2009, 50, 5633. (e) Haubenreissera, S.; Niggemann, M. Adv. Synth. Catal. 2011, 353, 469. (f) Das, B. G.; Nallagonda, R.; Ghorai, P. J. Org. Chem. 2012, 77, 5577.
[6] (a) Ozawa, F.; Okamoto, H.; Kawagishi, S.; Yamamoto, S.; Minami, T.; Yoshifuji, M. J. Am. Chem. Soc. 2002, 124, 10968. (b) Qin, H.; Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. Angew. Chem., Int. Ed. 2007, 46, 409. (c) Lu, Y.; Fu, X.; Chen, H.; Du, X.; Jia, X.; Liu, Y. Adv. Synth. Catal. 2009, 351, 1517. (d) Yamamoto, H.; Ho, E.; Namba, K.; Imagawa, H.; Nishizawa, M. Chem.-Eur. J. 2010, 16, 11271. (e) Ohshima, T.; Nakahara, Y.; Ipposhi, J.; Miyamotob, Y.; Mashima, K. Chem. Commun. 2011, 47, 8322.
[7] Fan, X.; Fu, L.-A.; Li, N.; Lv, H.; Cui, X.-M.; Qi, Y. Org. Biomol. Chem. 2013, 11, 2147.
[8] (a) Rubenbauer, P.; Bach, T. Adv. Synth. Catal. 2008, 350, 1125. (b) Powell, D. A.; Pelletier, G. Tetrahedron Lett. 2008, 49, 2495. (c) Feuerstein, M.; Laurenti, D.; Doucet, H.; Santelli, M. Tetrahedron Lett. 2001, 42, 2313. (d) Deng, H.-P.; Wei, Y.; Shi, M. Eur. J. Org. Chem. 2011, 1956.
[9] For selected reviews and examples see: (a) Speckamp, W. N.; Moolenaar, M. J. Tetrahedron 2000, 56, 3817. (b) Maryanoff, B. E.; Zhang, H.-C.; Cohen, J. H.; Turchi, I. J.; Maryanoff, C. A. Chem. Rev. 2004, 104, 1431. (c) Kinderman, S. S.; Wekking, M. M. T.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. J. T. J. Org. Chem. 2005, 70, 5519. (d) Raheem, I. T.; Thiara, P. S.; Peterson, E. A.; Jacobsen, E. N. J. Am. Chem. Soc. 2007, 129, 13404. (e) Pin, F.; Comesse, S.; Garrigues, B.; Marchalin, Š.; Daïch, A. J. Org. Chem. 2007, 72, 1181. (f) Muratore, M. E.; Holloway, C. A.; Pilling, A. W.; Storer, R. I.; Ttevitt, G.; Dixon, D. J. J. Am. Chem. Soc. 2009, 131, 10796. (g) Martínez-Estibalez, U.; Gómez-SanJuan, A.; García-Calvo, O.; Aranzamendi, E.; Lete, E.; Sotomayor, N. Eur. J. Org. Chem. 2011, 3610. (h) Che, J.; Liu, Q.; Dai, X. Y.; Nie, L. L.; Wu, X. Y. Chin. J. Org. Chem. 2013, 33, 1 (in Chinese). (陈杰, 刘钦, 戴小鸯, 聂凛凛, 房辉辉, 吴小余, 有机化学, 2013, 33, 1.) (i) Ran, L. F.; Liang, H.; Guan, Z. H. Chin. J. Org. Chem. 2013, 33, 66 (in Chinese). (冉陇飞, 梁浩, 关正辉, 有机化学, 2013, 33, 66.) (j) Du, L.; Cao, P.; Liao, J. Acta Chim. Sinica 2013, 71, 1239 (in Chinese). (杜乐, 曹鹏, 廖建, 化学学报, 2013, 71, 1239.) (k) Nie, H. F.; Zhou, H. Y.; Li, X. N.; Li, Y. Q.; Wang, J. X. Chin. J. Org. Chem. 2013, 33, 2412 (in Chinese). (聂红芬, 周宏勇, 李小娜, 李云庆, 王家喜, 有机化学, 2013, 33, 2412.)
[10] (a) Carter, D. S.; Van Vranken, D. L. J. Org. Chem. 1999, 64, 8537. (b) Gunawan, S.; Hulme, C. Tetrahedron Lett. 2013, 54, 4467. (c) La Venia, A.; Lemrova, B.; Krchnak, V. ACS Comb. Sci. 2013, 15, 59.
[11] (a) Tsuchimoto, T.; Ozawa, Y.; Negoro, R.; Shirakawa, E.; Kawakami, Y. Angew. Chem. Int. Ed. 2004, 43, 4231. (b) Mentink, G.; van Maarseveen, J. H.; Hiemstra, H. Org. Lett. 2002, 4, 3497. (c) Othman, R. B.; Bousquet, T.; Othman, M.; Dalla, V. Org. Lett. 2005, 7, 5335. (d) Shirakawa, E.; Uchiyama, N.; Hayashi, T. J. Org. Chem. 2011, 76, 25. (e) Sun, M.-M.; Zhang, T.-S.; Bao, W.-L. J. Org. Chem. 2013, 78, 8155. (f) Xu, H.-Y.; Wang, S.-Y.; Jiang, R.; Xu, X.-P.; Chu, X.-Q.; Ji, S.-J. Tetrahedron 2012, 68, 8340.
[12] (a) Akiyama, S.; Niki, T.; Utsunomiya, T.; Watanabe, J.; Nishioka, M.; Suzuki, H.; Hayasaka, F.; Yamagishi, K. EP 1020447, 2000 [Chem. Abstr. 1999, 130, 237562]. (b) Gobert, J.; Giurgea, C.; Geerts, J.-P.; Bodson, G. EP 165919, 1985 [Chem. Abstr. 1986, 105, 97305]. (c) Kenda, B.; Quesnel, Y.; Ates, A.; Michel, P.; Turet, L.; Mercier, J. WO 2006128693, 2006 [Chem. Abstr. 2006, 146, 27722]. (d) Kenda, B.; Michel, P.; Quesnel, Y. WO 2005054188, 2005 [Chem. Abstr. 2005, 143, 59977]. (e) Gobert, J.; Geerts, J.-P.; Bodson, G. EP 0162036, 1985 [Chem. Abstr. 1985, 105, 18467]. (f) Schmiesing, R. J.; Murray, R. J. US 5334720, 1994 [Chem. Abstr. 1995, 122, 81126]. (g) Gouliaev, A. H.; Senning, A. Brain Res. Rev. 1994, 19, 180. (h) Ramachandran, G.; Karthikeyan, N. S.; Giridharan, P.; Sathiyanarayanan, K. I. Org. Biomol. Chem. 2012, 10, 5343.
[13] (a) Nishimura, Y. In Studies in Natural Products Chemistry, Vol. 16, Ed.: Atta-ur-Rahman, Elsevier, Amsterdam, 1995, 75. (b) Fletcher, M. D.; Campbell, M. M. Chem. Rev. 1998, 98, 763. (c) Kingsbury, W. D.; Boehm, J. C.; Perry, D.; Gilvary, C. Proc. Natl. Acad. Sci. U. S. A. 1984, 81, 4573. (d) Hwang, S. Y.; Berges, D. A.; Taggart, J. J.; Gilvarg, C. J. Med. Chem. 1989, 32, 694. (e) Nishimura, Y.; Shitara, E.; Adachi, H.; Toyoshima, M.; Nakajima, M.; Okami, Y.; Takeuchi, T. J. Org. Chem. 2000, 65, 2. (f) Lepper, E. R.; Ng, S. W.; Gutschow, M.; Weiss, M.; Hauschildt, S.; Hecker, T. K.; Luzzio, F. A.; Eger, K.; Figg, W. D. J. Med. Chem. 2004, 47, 2219.
[14] (a) Goodman, M.; Chorev, M. Acc. Chem. Res. 1979, 12, 1. (b) Chorev, M.; Goodman, M. Acc. Chem. Res. 1993, 26, 266. (c) Chorev, M.; Willson, C. G.; Goodman, M. J. Am. Chem. Soc. 1977, 99, 8075. (d) Moutevelis-Minakakis, P.; Photaki, I. J. J. Chem. Soc., Perkin Trans. 1 1985, 2277. (e) Katritzky, A. R.; Urogdi, L.; Mayence, A. J. Org. Chem. 1990, 55, 2206. (f) Zhao, M.; Kleinman, H. K.; Mokotoff, M. J. Pept. Res. 1997, 49, 240.
[15] (a) Rowland, G. B.; Zhang, H.; Rowland, E. B.; Chennamadhavuni, S.; Wang, Y.; Antilla, J. C. J. Am. Chem. Soc. 2005, 127, 15696. (b) Liang, Y.; Rowland, E. B.; Rowland, G. B.; Perman, J. A.; Antilla, J. C. Chem. Commun. 2007, 4477. (c) Cheng, X.; Vellalath, S.; Goddard, R.; List, B. J. Am. Chem. Soc. 2008, 130, 15786.
[16] 16. Zhu, S. J.; Dong, J.; Fu, S. M.; Jiang, H. F.; Zeng, W. Org. Lett. 2011, 13, 4914.
[17] (a) Barker, J.; Kilner, M. Coord. Chem. Rev. 1994, 133, 219. (b) Lee, M. Y.; Kim, M. H.; Kim, J.; Kim, S. H.; Kim, B. T.; Jeong, I. H.; Chang, S.; Kim, S. H.; Chang, S.-Y. Bioorg. Med. Chem. Lett. 2010, 20, 541. (c) Vernier, W.; Chong, W.; Rewolinski, D.; Greasley, S.; Pauly, T.; Shaw, M.; Dinh, D.; Ferre, R. A.; Nukui, S.; Ornelas, M.; Reyner, E. Bioorg. Med. Chem. 2010, 18, 3307. (d) Al-Said, M. S.; Ghorab, M. M.; Al-Dosari, M. S.; Hamed, M. M. Eur. J. Med. Chem. 2011, 46, 201.(a) Gonzlez, A. S.; Arrays, R. G.; Carretero, J. C. Org. Lett. 2006, 8, 2977. (b) Morimoto, H.; Lu, G.; Aoyama, N.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2007, 129, 9588.

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