Chinese Journal of Organic Chemistry >
Progress of Mitsunobu Reaction in Construction of Chemical Bonds
Received date: 2014-06-04
Revised date: 2014-08-29
Online published: 2014-09-18
Supported by
Project supported by the Qing Lan Talent Engineering Funds of Lanzhou Jiaotong University (No. QL-06-01A).
The Mitsunobu reaction is an effective method for making a new chemical bond by condensation of an alcohol with an acidic compound. It can be applied for the construction of C—O, C—N, C—S and C—C bonds, and has been widely used in the synthesis of natural products and functional organic molecules. In this review, the mechanism of the Mitsunobu reaction and its application in the construction of chemical bonds are introduced. Moreover, the regioselectivity of this reaction is systematically summarized.
Wang Xiaolong , Yang Fang , Xue Ziyan , Wang Xiaoqiang . Progress of Mitsunobu Reaction in Construction of Chemical Bonds[J]. Chinese Journal of Organic Chemistry, 2015 , 35(1) : 29 -38 . DOI: 10.6023/cjoc201406003
[1] Mitsunobu, O. Synthesis 1981, 1.
[2] Swamy, K. C. K.; Kumar, N. N. B.; Balaraman, E.; Kumar, K. V. P. P. Chem. Rev. 2009, 109, 2551.
[3] Reynolds, A. J.; Kassiou, M. Curr. Org. Chem. 2009, 13, 1610.
[4] Hughes, D. L. Org. Prep. Proced. Int. 1996, 28, 127.
[5] But, T. Y. S.; Toy, P. H. Chem. Asian J. 2007, 2, 1340.
[6] Ren, X. F.; Xu, J. L.; Chen, S. H. Chin. J. Org. Chem. 2006, 26, 454 (in Chinese). (任新锋, 徐菁利, 陈思浩, 有机化学, 2006, 26, 454.)
[7] Figlus, M.; Wellaway, N.; Cooper, A. W. J.; Sollis, S. L.; Hartley, R. C. ACS Comb. Sci. 2011, 13, 280.
[8] Michigami, K.; Hayashi, M. Tetrahedron 2012, 68, 1092.
[9] Schenk, S.; Weston, J.; Anders, E. J. Am. Chem. Soc. 2005, 127, 12566 and references therein.
[10] Swamy, K. C. K.; Kumar, K. P.; Kumar, N. N. B. J. Org. Chem. 2006, 71, 1002.
[11] (a) Ahn, C.; Correia, R.; DeShong, P. J. Org. Chem. 2002, 67, 1751. (b) Ahn, C.; DeShong, P. J. Org. Chem. 2002, 67, 1754.
[12] Fitzjarrald, V. P.; Pongdee, R. Tetrahedron Lett. 2007, 48, 3553.
[13] Perali, R. S.; Mandava, S.; Chunduri, V. R. Tetrahedron Lett. 2011, 52, 3045.
[14] Huang, J.; Yang, J. R.; Zhang, J.; Yang, J. J. Am. Chem. Soc. 2012, 134, 8806.
[15] ?nie?ek, M.; Stecko, S.; Panfil, I.; Furman, B.; Chmielewski, M. J. Org. Chem. 2013, 78, 7048.
[16] (a) Ting, S. Z. Y.; Baird, L. J.; Dunn, E.; Hanna, R.; Leahy, D.; Chan, A.; Miller, J. H.; Teesdale-Spittle, P. H.; Harvey, J. E. Tetrahedron 2013, 69, 10581. (b) Venkanna, A.; Sreedhar, E.; Siva, B.; Babu, K. S.; Prasad, K. R.; Rao, J. M. Tetrahedron: Asymmetry 2013, 24, 1010.
[17] Williams, B. D.; Smith, A. B. Org. Lett. 2013, 15, 4584.
[18] (a) Lanning, M. E.; Fletcher, S. Tetrahedron Lett. 2013, 54, 4624. (b) Yang, J.; Dai, L.; Wang, X.; Chen, Y. Tetrahedron 2011, 67, 1456.
[19] Trost, B. M.; Quintard, A. Angew. Chem., Int. Ed. 2012, 51, 6704.
[20] Krysiak, J. M.; Kreuzer, J.; Macheroux, P.; Hermetter, A.; Sieber, S. A.; Breinbauer, R. Angew. Chem., Int. Ed. 2012, 51, 7035.
[21] Lan, P.; Banwell, M. G.; Willis, A. C. J. Org. Chem. 2014, 79, 2829.
[22] Lu, P.; Gu, Z.; Zakarian, A. J. Am. Chem. Soc. 2013, 135, 14552.
[23] Caras-Quintero, D.; Bäuerle, P. Chem. Commun. 2002, 2690.
[24] Xu, Z.; Kang, J. H.; Wang, F.; Paek, S. M.; Hwang, S. J.; Kim, Y.; Kim, S. J.; Choy, J. H.; Yoon, J. Tetrahedron Lett. 2011, 52, 2823.
[25] García-Delgado, N.; Riera, A.; Verdaguer, X. Org. Lett. 2007, 9, 635.
[26] Samanta, K.; Srivastava, N.; Saha, S.; Panda, G. Org. Biomol. Chem. 2012, 10, 1553.
[27] Lee, J. C.; Francis, S.; Dutta, D.; Gupta, V.; Yang, Y.; Zhu, J.-Y.; Tash, J. S.; Schönbrunn, E.; Georg, G. I. J. Org. Chem. 2012, 77, 3082.
[28] Wallentin, C.-J.; Nguyen, J. D.; Finkbeiner, P.; Stephenson, C. R. J. J. Am. Chem. Soc. 2012, 134, 8875.
[29] Maharvi, G. M.; Fauq, A. H. Tetrahedron Lett. 2010, 51, 6542.
[30] Suetsugu, S.; Nishiguchi, H.; Tsukano, C.; Takemoto, Y. Org. Lett. 2014, 16, 996.
[31] Li, Q.; Li, G.; Ma, S.; Feng, P.; Shi, Y. Org. Lett. 2013, 15, 2601.
[32] Ma, C.; Gu, J.; Teng, B.; Zhou, Q.-Q.; Li, R.; Chen, Y.-C. Org. Lett. 2013, 15, 6206.
[33] Green, J. E.; Bender, D. M.; Jackson, S.; O'Donnell, M. J.; McCarthy, J. R. Org. Lett. 2009, 11, 807.
[34] Gómez-Vidal, J. A.; Silverman, R. B. Org. Lett. 2001, 3, 2481.
[35] Busto, E.; Gotor-Fernández, V.; Gotor, V. J. Org. Chem. 2012, 77, 4842.
[36] (a) Kalita, M.; Cingarapu, S.; Roy, S.; Park, S. C.; Higgins, D.; Jankowiak, R.; Chikan, V.; Klabunde, K. J.; Bossmann, S. H. Inorg. Chem. 2012, 51, 4521. (b) Jiang, B.; Wang, J.; Huang, Z. Org. Lett. 2012, 14, 2070.
[37] Morita, N.; Krause, N. Eur. J. Org. Chem. 2006, 13, 4634.
[38] Petit, S.; Azzouz, R.; Fruit, C.; Bischoff, L.; Marsais, F. Tetrahedron Lett. 2008, 49, 3663.
[39] Babij, N. R.; Wolfe, J. P. Angew. Chem., Int. Ed. 2012, 51, 4128.
[40] Wang, X. L.; Liu, D.; Xia, Y. M.; Cao, X. P.; Pan, X. F. Chin. J. Chem. 2004, 22, 467.
[41] Gärtner, M.; Kossler, D.; Pflästerer, D.; Helmchen, G. J. Org. Chem. 2012, 77, 4491.
[42] Hillier, M. C.; Desrosiers, J. N.; Marcoux, J. F.; Grabowski, E. J. J. Org. Lett. 2004, 6, 573.
[43] Prakash, G. K. S.; Chacko, S.; Alconcel, S.; Stewart, T.; Mathew, T.; Olah, G. A. Angew. Chem., Int. Ed. 2007, 46, 4933.
[44] Ko, S. Y. J. Org. Chem. 2002, 67, 2689.
[45] Gravotto, G.; Chimichi, S.; Robaldo, B.; Boccalini, M. Tetrahedron Lett. 2003, 44, 8383.
[46] Wang, X. L.; Ju, T. T.; Li, X. D. Cao, X. P. Synlett 2010, 19, 2947.
[47] Dunford, D. G.; Chaudhry, F.; Kariuki, B.; Knight, D. W.; Wheeler, R. C. Tetrahedron Lett. 2012, 53, 7006.
[48] Tahir, H.; Hindsgaul, O. J. Org. Chem. 2000, 65, 911.
[49] Appendino, G.; Minassi, A.; Daddario, N.; Bianchi, F.; Tron, G. C. Org. Lett. 2002, 4, 3839.
[50] Wang, G.; Ella-Menye, J. R.; Martin, M. S.; Yang, H.; Williams, K. Org. Lett. 2008, 10, 4203.
[51] Wang, X. L.; Ma, Y. Y.; Ju, T. T. J. Chem. Res. 2013, 7, 417.
[52] Fletcher, S.; Shahani, V. M.; Gunning, P. T. Tetrahedron Lett. 2009, 50, 4258.
[53] Chen, L.; Fletcher, S. Tetrahedron Lett. 2014, 55, 1693.
[54] (a) Krohn, K.; Ahmed, I.; John, M. Synthesis 2009, 5, 779. (b) Krohn, K.; Ahmed, I.; John, M.; Letzel, M. C.; Kuck, D. Eur. J. Org. Chem. 2010, 13, 2544.
[55] Azzouz, R.; Fruit, C.; Bischoff, L.; Marsais, F. J. Org. Chem. 2008, 73, 1154.
[56] (a) Kim, Y. W.; Hackett, J. C.; Brueggemeier, R. W. J. Med. Chem. 2004, 47, 4032. (b) Su, B.; Hackett, J. C.; Díaz-Cruz, E. S.; Kim, Y. W.; Brueggemeier, R. W. Bioorg. Med. Chem. 2005, 13, 6571.
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