Chinese Journal of Organic Chemistry >
Progress in Separation-Friendly Mitsunobu Reactions
Received date: 2016-06-20
Revised date: 2016-07-26
Online published: 2016-08-12
The Mitsunobu reaction is famous for its mild conditions, good stereoselectivities and extensive applications. But it is also infamous for difficult purification in organic synthetic chemistry, because of the formation of by-products such as phosphine oxide and hydrazine derivatives. To simplify the separation and improve the efficiency of purification is a hot topic in the research of Mitsunobu reaction. Various emerging strategies for product isolation in Mitsunobu reactions are reviewed. Special stress is laid on the principle, advantages and disadvantages of these strategies.
Key words: Mitsunobu reaction; separation strategy; simplified separation
Qi Na , Guo Jian , He Yun . Progress in Separation-Friendly Mitsunobu Reactions[J]. Chinese Journal of Organic Chemistry, 2016 , 36(12) : 2880 -2887 . DOI: 10.6023/cjoc201606029
[1] Swamy, K. C. K.; Kumar, N. N. B.; Balaraman, E.; Kumar, K. V. P. P. Chem. Rev. 2009, 109, 2551.
[2] Mitsunobu, O. Synthesis 1981, 1.
[3] Dandapani, S.; Curran, D. P. Chem. Eur. J. 2004, 10, 3130.
[4] Dembinski, R. Eur. J. Org. Chem. 2004, 2763.
[5] Arnold, L. D.; Assil, H. I.; Vederas, J. C. J. Am. Chem. Soc. 1989, 111, 3973.
[6] Tunoori, A. R.; Dutta, D.; Georg, G. I. Tetrahedron Lett. 1998, 39, 8751.
[7] Jr. Wentworth, P.; Vandersteen, A. M.; Janda, K. D. Chem. Commun. 1997, 759.
[8] Charette, A. B.; Janes, M. K.; Boezio, A. A. J. Org. Chem. 2001, 66, 2178.
[9] Camp, D.; Jenkins, I. D. Aust. J. Chem. 1988, 41, 1835.
[10] Itzstein, M. V.; Mocerino, M. Synth. Commun. 1990, 2049.
[11] Kiankarimi, M.; Lowe, R.; Mccarthy, J. R.; Whitten, J. P. Tetrahedron Lett. 1999, 40, 4497.
[12] Pelletier, J. C.; Kincaid, S. Tetrahedron Lett. 2000, 41, 797.
[13] Starkey, G. W.; Parlow, J. J.; Flynn, D. L. Bioorg. Med. Chem. Lett. 1998, 8, 2385.
[14] Yoakim, C.; Guse, I.; O'Meara, J. A.; Thavonekham, B. Synlett 2003, 473.
[15] Jackson, T.; Routledge, A. Tetrahedron Lett. 2003, 44, 1305.
[16] Dobbs, A. P.; Mcgregor-Johnson, C. Tetrahedron Lett. 2002, 43, 2807.
[17] Dandapani, S.; Curran, D. P. Tetrahedron 2002, 58, 3855.
[18] Dandapani, S.; Curran, D. P. J. Org. Chem. 2004, 69, 8751.
[19] Chu, Q.; Henry, C.; Curran, D. P. Org. Lett. 2008, 10, 2453.
[20] Barrett, A. G. M.; Roberts, R. S.; Schröder, J. Org. Lett. 2000, 2, 2999.
[21] Harned, A. M.; He, H. S.; Toy, P. H.; Flynn, D. L.; Hanson, P. R. J. Am. Chem. Soc. 2004, 127, 52.
[22] Maity, P. K.; Rolfe, A.; Samarakoon, T. B.; Faisal, S.; Kurtz, R. D.; Long, T. R.; Schätz, A.; Flynn, D. L.; Grass, R. N.; Stark, W. J.; Reiser, O.; Hanson, P. R. Org. Lett. 2011, 13, 8.
[23] Maity, P. K.; Kainz, Q. M.; Faisal, S.; Rolfe, A.; Samarakoon, T. B.; Basha, F. Z.; Reiser, O.; Hanson, P. R. Chem. Commun. 2011, 47, 12524.
[24] Lan, P.; Porco, J. A.; South, M. S.; Parlow, J. J. J. Comb. Chem. 2003, 5, 660.
[25] Sugimura, T.; Hagiya, K. Chem. Lett. 2007, 36, 566.
[26] Hagiya, K.; Muramoto, N.; Misaki, T.; Sugimura, T. Tetrahedron 2009, 65, 6109.
[27] Figlus, M.; Wellaway, N.; Cooper, A. W. J.; Sollis, S. L.; Hartley, R. ACS Comb. Sci. 2011, 13, 280.
[28] Iranpoor, N.; Firouzabadi, H.; Khalili, D.; Motevalli, S. J. Org. Chem. 2008, 73, 4882.
[29] Yang, J.; Dai, L.; Wang, X.; Chen, Y. Tetrahedron 2011, 67, 1456.
[30] Furkert, D. P.; Breitenbach, B.; Juen, L.; Sroka, I.; Pantin, M.; Brimble, M. A. Eur. J. Org. Chem., 2014, 7806.
[31] Aronov, A. M.; Gelb, M. H. Tetrahedron Lett. 1998, 39, 4947.
[32] Su, S.; Giguere, J. R.; Schaus, S. E.; Porco, Jr., J. Tetrahedron 2004, 60, 8645.
[33] Markowicz, M. W.; Dembinski, R. Org. Lett. 2002, 4, 3785.
[34] Guo, J.; Lu, Y.; Zhang, L.; Ye, X.-S. Synlett 2012, 23, 1696.
[35] Harned, A. M.; Hanson, P. R. Org. Lett. 2002, 4, 1007.
[36] Muramoto, N.; Yoshino, K.; Misaki, T.; Sugimura, T. Synthesis 2013, 45, 931.
[37] But, T. Y. S.; Toy, P. H. J. Am. Chem. Soc. 2006, 128, 9636.
[38] But, T. Y. S.; Lu, J.; Toy, P. H. Synlett 2010, 1115.
[39] Hirose, D.; Taniguchi, T.; Ishibashi, H. Angew. Chem., Int. Ed. 2013, 52, 4613.
[40] Buonomo, J. A.; Aldrich, C. C. Angew. Chem., Int. Ed. 2015, 54, 13041.
[41] Hirose, D.; Gazvoda, M.; Kosmrlj, J.; Taniguchi, T. Chem. Sci. 2016, 7, 5148.
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