B-podands as efficient catalysts for the ring opening of epoxides in water: A versatile and atom economical method for the synthesis of vicinal azidoalcohols
الموضوعات : Iranian Journal of CatalysisAli Kiasat 1 , Fakhri Ataeian 2 , Mehdi Fallah-Mehrjardi 3
1 - Department of Chemistry, College of Science, Shahid Chamran University, Ahvaz 61357-4-3169, I.R. Iran.
2 - Department of Chemistry, College of Science, Shahid Chamran University, Ahvaz 61357-4-3169, I.R. Iran.
3 - Department of Marine Chemistry, Khorramshahr University of Marine Science and Technology, Khorramshahr 669, I.R. Iran.
الکلمات المفتاحية: 1, Ring Opening, Phase transfer catalyst, B-podands, 2-Azidoalcohol, Epoxide, Atom economic,
ملخص المقالة :
For the first time B-podands have been studied as an efficient and powerful catalysts in the ring opening of epoxides with azide anion in water. The reaction afforded the corresponding 1,2-azidoalcohols with high regioselectivity under mild reaction conditions and in a highly atom economic fashion.
[1] A. R. Kiasat, M. Fallah-Mehrjardi, Catal. Commun. 9 (2008) 1497-1500.
[2] J. Chen, S. K. Spear, J. Huddleston, G. R. D Rogers, Green Chem. 7 (2005) 64-82.
[3] U. Sachin, M. C. Sonavane, S. Khalil, J. Almog, Y. Sasson, Tetrahedron Lett. 49 (2008) 520-522.
[4] Y. S. Park, H. J. Kim, D. Lim, Bull. Korean Chem. Soc. 22 (2001) 958-962.
[5] S. Kotha, A. C. Deb, S. Chattopadhyay, Lett. Org. Chem. 3 (2006) 128-134.
[6] A. R. Kiasat, M. Fallah-Mehrjardi, Bull. Korean Chem. Soc. 29 (2008) 2346-2348.
[7] B. Thierry, J. C. Plaquevent, D. Cahard, Mol. Divers. 9 (2005) 277-290.
[8] B. Leska, R. Pankiewicz, G. Schroeder, A. Maia, Tetrahedron Lett. 47 (2006) 5673-5676.
[9] B. Leska, R. Pankiewicz, G. Schroeder, A. Maia, J. Mol. Catal. 269 (2007) 141-148.
[10] H. Lehmkuhl, R. Farroch, K. Hauschild, Synthesis 3 (1977) 184-185.
[11] E. F. V. Scriven, K. Turnbull, Chem. Rev. 88 (1988) 297-368.
[12] S. J. Gorzynski, Synthesis (1984) 629-656.
[13] D. M. Coe, P. L. Myers, D. M. Parry, S. M. Roberts, R. Storer, J. Chem. Soc. Chem. Commun. (1990) 151-153.
[14] B. T. Smith, V. Gracias, J. Aube, J. Org. Chem. 65 (2000) 3771-3774.
[15] J. G. Badiang, J. Aube, J. Org. Chem. 61 (1996) 2484-2487.
[16] B. T. Cho, S. K. Kang, S. H. Shin, Tetrahedron Asym. 13 (2002) 1209-1217.
[17] K. B. Hansen, J. L. Leighton, E. N. Jacobsen, J. Am. Chem. Soc. 118 (1996) 10924-10925.
[18] N. Iranpoor, F. Kazemi, Synth. Commun. 29 (1999) 561-566.
[19] F. Kazemi, A. R. Kiasat, S. Ebrahimi, Synth. Commun. 33(2003) 999-1004.
[20] B. Yadollahi, H. Danafar, Catal. Lett. 113 (2007) 120-123.
[21] B. Tamami, H. Mahdavi, Tetrahedron Lett. 42 (2001) 8721-8724.
[22] A. R. Kiasat, R. Badri, B. Zargar, S. Sayyahi, J. Org. Chem. 73 (2008) 8382-8385.
[23] A. R. Kiasat, M. Zayadi, Catal. Commun. 9 (2008) 2063-2067.
[24] G. Schroeder, B. Gierczyk, B. Leska, J. Incl. Phenom. 35 (1999) 327-334.
[25] S. Saito, S. Yamashita, T. Nishikawa, Y. Yokoyama, T. Moriwake, Tetrahedron Lett. 30 (1989) 4153-4156.
[26] G. Sabitha, R. S. Babu, M. Rajkumar, J. S. Yadav, Org. Lett. 4 (2002) 343-345.
