Progress of Mitsunobu Reaction in Construction of Chemical Bonds

doi:10.6023/cjoc201406003

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (1): 29-38.DOI: 10.6023/cjoc201406003 Previous Articles Next Articles

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Mitsunobu反应在构建化学键中的研究进展

王小龙, 杨芳, 薛自燕, 王晓强

兰州交通大学化学与生物工程学院兰州 730070

收稿日期:2014-06-04 修回日期:2014-08-29 发布日期:2014-09-18
通讯作者: 王小龙 E-mail:wangxl@mail.lzjtu.cn
基金资助:
兰州交通大学青蓝人才工程基金(No. QL-06-01A)资助项目.

Progress of Mitsunobu Reaction in Construction of Chemical Bonds

Wang Xiaolong, Yang Fang, Xue Ziyan, Wang Xiaoqiang

School of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070

Received:2014-06-04 Revised:2014-08-29 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.

Key words: Mitsunobu reaction, chemical bond, reaction mechanism, stereoselectivity, regioselectivity

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Wang Xiaolong, Yang Fang, Xue Ziyan, Wang Xiaoqiang. Progress of Mitsunobu Reaction in Construction of Chemical Bonds[J]. Chin. J. Org. Chem., 2015, 35(1): 29-38.

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References

[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.

Mitsunobu反应在构建化学键中的研究进展

Progress of Mitsunobu Reaction in Construction of Chemical Bonds

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