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Chinese Journal of Organic Chemistry >

2012 , Vol. 32 >Issue 05: 825 - 833

DOI: https://doi.org/10.6023/cjoc1110053

Reviews

Progress in the Synthesis and Application of Sulfoximines

  • Wang Yaya ,
  • Hong Xuechuan ,
  • Deng Zixin
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  • Key Laboratory of Combinatorial Biosynthesis and Drug Discovery, Ministry of Education, School of Pharmaceutical Sciences, Wuhan University, Wuhan 430071

Received date: 2011-10-05

  Revised date: 2011-11-30

  Online published: 2011-12-14

Supported by

Project supported by the Fund of State Key Laboratory of Phytochemistry and Plant Resources in West China (No. P2010-KF10), the Specialized Research Fund of the Doctoral Program of Higher Education (No. 20110141120017), and the National Natural Science Foundation of China (No. 81102357).

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Abstract

Sulfoximines are a very important class of heteroatom substitutional compounds and have attracted considerable interest. This review deals with methods for the synthesis of sulfoximines and their applications in catalytical asymmetric synthesis, bioactive small molecules synthesis and total synthesis of natural products. The developing trend and prospects for future application of sulfoximines compound are discussed.

Key words： sulfoximines; synthesis; application; asymmetric catalysis; total synthesis

Cite this article

Wang Yaya , Hong Xuechuan , Deng Zixin . Progress in the Synthesis and Application of Sulfoximines[J]. Chinese Journal of Organic Chemistry, 2012 , 32(05) : 825 -833 . DOI: 10.6023/cjoc1110053

References

[1] (a) Whitehead, J. K.; Bentley, H. R. J. Am. Chem. Soc. 1952, 1572.(b) Bentley, H. R.; McDermott, E. E.; Pace, J.; Whitehead, J. K.;Moran, T. Nature 1950, 165.

[2] (a) Griffith, O. W.; Meister, A. J. Biol. Chem. 1979, 254, 7558.(b) Bailey, H. H. Chem.-Biol. Interact. 1998, 8, 23.(c) O'Dwyer, P. J.; Hamilton, T. C.; LaCreta, F. P.; Gallo, J. M.;Kilpatrick, D.; Halbherr, T.; Brennan, J.; Bookman, M. A.; Hoffman,J.; Young, R. C.; Comis, R. L.; Ozols, R. F. J. Clin. Oncol.1996, 14, 249.(d) Mueller, E. US 4442111, 1984 [Chem. Abstr. 1983, 98,215493].

[3] (a) Johnson, C. R. Acc. Chem. Res. 1973, 6, 341.(b) Pyne, S. G. Sulfur Rep. 1992, 12, 57.(c) Reggelin, M.; Zur, C. Synthesis 2000, 1.

[4] (a) Mikolajczyk, M. Synthsis 1990, 937.(b) Kinahan, T. C.; Tye, H. Tetrahedron: Asymmetry 2001, 12,1255.(c) Johnson, C. R.; Keiser, J. E. Org. Synth. 1966, 46, 78.(d) Furukawa, N.; Akutagawa, K.; Yoshimura, T.; Oae, S. Synthesis1982, 77.(e) Chen, C.-Y.; Li, Y.; Xiao, Y.; Zhu, L.; Cheng, C.-M.; Liu, Y.Chin. J. Org. Chem. 2011, 31, 925 (in Chinese ).(陈春玉, 李毅, 肖英, 朱林, 程长明, 刘杨, 有机化学, 2011, 31,925.)

[5] Johnson, C. R. J. Am. Chem. Soc. 1970, 92, 6594.

[6] Brandt, J.; Gais, H. J. Tetrahedron: Asymmetry 1997, 8, 909.

[7] Okamura, H.; Bolm, C. Org. Lett. 2004, 6, 1305.

[8] (a) Mancheno, O. G.; Bolm, C. Org. Lett. 2006, 8, 2349.(b) Johnson, C. R.; Kirchhoff, R. A.; Corkins, H. G. J. Org. Chem.1974, 39, 2459

[9] Mancheno, O. G.; Bolm, C. Org. Lett 2009, 11, 2429.

[10] Cho, G. Y.; Bolm, C. Org. Lett. 2005, 7, 4983.

[11] (a) Mancheno, O. G.; Bistri, O.; Bolm, C. Org. Lett. 2007, 9, 3809.(b) Ochiai, M.; Naito, M.; Miyamoto, K.; Hayashi, S.; Nakanishi,W. Chem. Eur. J. 2010, 16, 8713.

[12] Siu, T.; Yudin, A. K. Org. Lett. 2002, 4, 1839.

[13] Bolm, C.; Muller, J. J. Am. Chem. Soc. 1993, 182.

[14] Bolm, C.; Simic, O.; Martin, M. Synlett 2001, 1878.

[15] Bolm, C.; Simic, O. J. Am. Chem. Soc. 2001, 123, 3830.

[16] Bolm, C.; Martin, M. Org. Lett. 2003, 5, 427.

[17] Harmata, M.; Ghosh, S. K. Org. Lett 2001, 3, 3321.

[18] Langner, M.; Bolm, C. Angew. Chem., Int. Ed. 2004, 43, 5984.

[19] (a) Remy, P.; Langner, M.; Bolm, C. Org. Lett. 2006, 8, 1209.(b) Kingsbury, J. S.; Corey, E. J. J. Am. Chem. Soc. 2005, 127,13813.

[20] Frings, M.; Bolm, C. Chem. Eur. J. 2010, 16, 4577.

[21] Steurer, M.; Bolm, C. J. Org. Chem. 2010, 75, 3301.

[22] Zecchini, G. P.; Paradisi, M. P.; Torrini, I.; Lucente, G.; Gavuzzo,E.; Mazza, F.; Pochetti, G. Tetrahedron Lett. 1991, 32, 6779.

[23] (a) Moree, W. J.; Marel, G. A. V.; Liskamp, R. M. J. TetrahendronLett. 1991, 32, 409.(b) Moree, W. J.; Marel, G. A. V.; Liskamp, R. J. J. Org. Chem.1996, 60, 5157.

[24] Morgan, B. P.; Scholtz, J. M.; Ballinger, M. D.; Zipkin, I. D.;Bartlett, P. A. J. Am. Chem. Soc. 1991, 113, 298

[25] (a) Mock, W. L.; Zhang, J. Z. J. Org. Chem. 1990, 55, 5791. (b) Mock, W. L.; Tsay, J. T. J. Am. Chem. Soc. 1989, 111, 4467.

[26] Bolm, C.; Kahmann, J. D.; Moll, D. Tetrahedron Lett. 1997, 38,1169.

[27] Bolm, C.; Muller, D.; Dalhn, D.; Hackenberger, C. P. R.;Weinhold, E. Bioorg. Med. Chem. Lett. 2003, 13, 3207.

[28] Cho, G. Y.; Okamura, H.; Bolm, C. J. Org. Chem. 2005, 70, 2346.

[29] (a) Virolleaud, M. A.; Sridharan, V.; Mailhol, D.; Rodriguez, J.Tetrahedron 2009, 65, 9756.(b) Sridharan, V.; Vologdin, N.; Virolleaud, M. A.; Rodriguez, J.Synthesis 2011, 2085.

[30] (a) Adrien, A.; Gais, H.-J.; K?hler, F.; Runsink, J.; Raabe, G. Org.Lett. 2007, 9, 2155.(b) Weinreb, S. M. Chem. Rev. 2006, 106, 2531.(c) Clive, D.; Yu, M.; Wang, J.; Yeh, V. S. C.; Kang, S. Chem. Rev.2005, 105, 4483.

[31] (a) Bund, J.; Gais, H.-J.; Schmitz, E.; Erdelmeier, I.; Raabe, G. Eur.J. Org. Chem. 1998, 1319.(b) Moncada, S.; Gryglewski, R.; Bunting, S.; Vane, J. R. Nature1976, 1, 263.

[32] Mahajan, V.; Gais, H. J. Chem. Eur. J. 2011, 17, 6187.

[33] Harmata, M.; Hong, X. C. J. Am. Chem. Soc. 2003, 125, 5754.

[34] Harmata, M.; Hong, X. C.; Barnes, C. L. Tetrahedron Lett. 2003,44, 7261.

[35] Harmata. M.; Hong. X. C. Tetrahedron Lett. 2005, 46, 3847.

[36] (a) Harmata, M.; Hong, X. C.; Barnes, C. L. Org. Lett. 2004, 6,2201.(b) Harmata. M.; Hong. X. C. Org. Lett. 2005, 7, 3581.(c) Johnson, T. W.; Corey, E. J. J. Am. Chem. Soc. 2001, 123, 4475.

[37] (a) Rodriguez, A. D.; Ramirez, C. J. Nat. Prod. 2001, 64, 100.(b) Rodriguez, A. D.; Ramirez, C.; Rodriguez, I. I.; Gonzalez, E.Org. Lett. 1999, 1, 527.
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