Enantioselective epoxidation of electron-deficient olefins: An organocatalytic approach

Chemical Record

Volumn 11, Issue 1, 2011, Pages 18-39

  Weiß, Katharina M ^a   Tsogoeva, Svetlana B ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

asymmetric epoxidation; electron deficient olefins; Juli Colonna epoxidation; organocatalysis; phase transfer catalysis

Indexed keywords

ALDEHYDE; ALKENE; EPOXIDE; KETONE;

ARTICLE; CATALYSIS; CHEMISTRY; ELECTRON; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; ALKENES; CATALYSIS; ELECTRONS; EPOXY COMPOUNDS; KETONES; STEREOISOMERISM;

EID: 79951486837     PISSN: 15278999     EISSN: 15280691     Source Type: Journal    
DOI: 10.1002/tcr.201000006     Document Type: Article

References (126)

1. A. Mannschreck, R. Kiesswetter, E. von Angerer, J. Chem. Educ. 2007, 84, 2012.
2. L. C. R. Pasteur, C R Hebd Seances Acad. Sci. 1848, 26, 535.
3. For an example on the application of Sharpless oxidation in the enantioselective synthesis of esomeprazole by employing the chiral ligand D-(-)-diethyl tartrate, see: P.L. Lindberg; S. von Unge, US patent 5714504, 1998.
4. (a), J.G. Smith, Synthesis 1984, 8, 629
5. (b) 2nd Ed. (Ed., I. Ojima,); Wiley, New York, 2000
6. (c), J. Marco-Contelles, M. T. Molina, S. Anjum, Chem. Rev. 2004, 104, 2857
7. (d) (Ed., J. E. Bäckvall,), Wiley-VCH, Weinheim, 2004
8. (e), Q.-H. Xia, H.-Q. Ge, C.-P. Ye, Z.-M. Liu, K.-X. Su,. Chem. Rev. 2005, 105, 1603.
9. For reviews, see: (a), P. Besse, H. Veschambre,. Tetrahedron 1994, 50, 8885
10. (b), C. Bonini, G. Righi,. Tetrahedron 2002, 58, 4981
11. (c), V. K. Aggarwal, C. L. Winn,. Acc. Chem. Res. 2004, 37, 611.
12. (a), A.-H. Li, L.-X. Dai, V. K. Aggarwal, Chem. Rev. 1997, 97, 2341
13. (b), A. Padwa, S. S. Murphree, ARKIVOC 2006, 6.
14. (a), H. B. Henbest, Chem. Soc. Spec. Publ. 1965, 19, 83
15. (b), K. P. Bryliakov, E. P. Talsi, S. N. Stas'ko, O. A. Kholdeeva, S. A. Popov, A. V. Tkachev, J. Mol. Catal. A: Chem. 2003, 194, 79.
16. (a), T. Katsuki, K. B Sharpless, J. Am. Chem. Soc. 1980, 102, 5974
17. (b), T. Katsuki, V. S. Martin, Org. React. 1996, 48, 1
18. (c), R. A. Johnson, K. B. Sharpless, in (Ed., I. Ojima,), Wiley-VCH, New York, 2000, Chapter 6
19. (d), T. Katsuki, in (Eds:, E. N. Jacobsen, A. Pfaltz, H. Yamamoto,), Springer, Berlin, 1999, pp. 621-648.
20. E. N. Jacobsen, in Catalytic Asymmetric Synthesis (Ed., I. Ojima,), Wiley-VCH, New York, 1993, Chapter 4.2.
21. T. Katsuki, Coord. Chem. Rev. 1995, 140, 189.
22. For reviews, see: (a), T. Nemoto, T. Ohshima, M. Shibasaki,. J. Synth. Org. Chem. Jpn 2002, 60, 94
23. (b), M. Shibasaki, M. Kanai, S. Matsunaga, Aldrichimica Acta 2006, 39, 31.
24. For reviews, see: (a), M. J. Porter, J. Skidmore,. Chem. Commun. 2000, 1215
25. (b), C. Lauret, S. M. Roberts, Aldrichimica Acta 2002, 35, 47
26. (c), D. R. Kelly, S. M. Roberts, Biopolymers 2006, 84, 74
27. (d), E. A. C. Davie, S. M. Mennen, Y. Xu, S. J. Miller, Chem. Rev. 2007, 107, 5759
28. (e), D. Díez, M. G. Núñez, A. B. Antón, P. García, R. F. Moro, N. M. Garrido, I. S. Marcos, P. Basabe, J. G. Urones, Curr. Org. Synth. 2008, 5, 186.
29. For recent general reviews, see: (a), P. I. Dalko, L. Moisan, Angew. Chem. Int. Ed. 2004, 43, 5138
30. (b) Special Issue on Asymmetric Organocatalysis: Acc. Chem. Res. 2004, 37
31. (c), A. Berkessel, H. Gröger, in, Wiley-VCH, Weinheim, 2005
32. (d) (Ed., P. I. Dalko,), Wiley-VCH, Weinheim, 2007.
33. For reviews, see: (a), W. Adam, C. R. Saha-Möller, P. A. Ganeshpure, Chem. Rev. 2001, 101, 3499
34. (b), Y. Shi, Acc. Chem. Res. 2004, 37, 488
35. (c), A. Armstrong, Angew. Chem. Int. Ed. 2004, 43, 1460
36. (d), A. Armstrong, D. R. Carbery, Annu. Rep. Prog. Chem, Sect B 2006, 102, 34
37. (e), G. Guillena, D. J. Ramón, Tetrahedron: Asymmetry 2006, 17, 1465
38. (f), E. M. McGarrigle, E. L. Myers, O. Illa, M. A. Shaw, S. L. Riches, V. K. Aggarwal, Chem. Rev. 2007, 107, 5841
39. (g), B. R. Buckley, Annu. Rep. Prog. Chem. Sect B 2007, 103, 90
40. (h), M. Seki, Synlett 2008, 164
41. (i), O. A. Wong, Y. Shi, Chem. Rev. 2008, 108, 3958.
42. T. Ooi, K. Maruoka, Angew. Chem. Int. Ed. 2007, 46, 4222.
43. For an example of galactonic acid synthesis, see:, P. C. Ray, S. M. Roberts, J. Chem. Soc., Perkin Trans. 1 2001, 149.
44. For an example of (+)-clausenamide synthesis, see:, M. W. Cappi, W.-P. Chen, R. W. Flood, Y.-W. Liao, S. M. Roberts, J. Skidmore, J. A. Smith, N. M. Williamson, Chem. Commun. 1998, 1159.
45. For an example of diltiazem und Taxol side chain synthesis, see:, B. M. Adger, J. V. Barkley, S. Bergeron, M. W. Cappi, B. E. Flowerdew, M. P. Jackson, R. McCague, T. C. Nugent, S. M. Roberts, J. Chem. Soc., Perkin Trans. 1 1997, 3501.
46. For an example of leukotriene synthesis, see:, J. R. Flisak, K. J. Gombatz, M. M. Holmes, A. A. Jarmas, I. Lantos, W. L. Mendelson, V. J. Novack, J. J. Remich, L. Snyder, J. Org. Chem. 1993, 58, 6247.
47. For selected examples of transformation of α,β-epoxy ketones into β-hydroxy ketones (aldol adducts), see:, G. A. Molander, G. Hahn, J. Org. Chem. 1986, 51, 2596.
48. For a comprehensive review on functionalization of α,β- epoxyketones to interesting intermediates, useful for the natural product synthesis, see:, C. Lauret, Tetrahedron: Asymmetry 2001, 12, 2359.
49. E. Weitz, A. Scheffer, Ber. Dtsch Chem. Ges. 1921, 54, 2327.
50. A. Lattanzi, Chem. Commun. 2009, 1452.
51. (a), S. Juliá, J. Masana, J. C. Vega, Angew. Chem. Int. Ed. 1980, 19, 929
52. (b), S. Juliá, J. Guixer, J. Masana, J. Rocas, S. Colonna, R. Annuziata, H. Molinari, J. Chem. Soc., Perkin Trans 1 1982, 1317
53. (c), S. Colonna, H. Molinari, S. Banfi, S. Juliá, J. Masana, A. Alvarez, Tetrahedron 1983, 39, 1635
54. (d), S. Banfi, S. Colonna, H. Molinari, S. Juliá, J. Guixer, Tetrahedron 1984, 40, 5207.
55. (a), W. Kroutil, P. Mayon, M. E. Lasterra-Sánchez, S. J. Maddrell, S. M. Roberts, S. R. Thornton, C. J. Todd, M. Tüter, Chem. Commun. 1996, 845
56. (b), P. A. Bentley, S. Bergeron, M. W. Cappi, D. E. Hibbs, M. B. Hursthouse, T. C. Nugent, R. Pulido, S. M. Roberts, L. E. Wu, Chem. Commun. 1997, 739
57. (c), T. Geller, S. M. Roberts, J. Chem. Soc., Perkin Trans 1 1999, 1397
58. (d), J. V. Allen, K.-H. Drauz, R. W. Flood, S. M. Roberts, J. Skidmore, Tetrahedron Lett. 1999, 40, 5417.
59. G. Licini, M. Bonchio, Q. B. Broxterman, B. Kaptein, A. Moretto, C. Toniolo, P. Scrimin, Biopolymers 2006, 84, 97.
60. (a), T. Geller, A. Gerlach, C. M. Krüger, H.-C. Militzer, Tetrahedron Lett. 2004, 45, 5065
61. (b), T. Geller, C. M. Krüger, H.-C. Militzer, Tetrahedron Lett. 2004, 45, 5069.
62. T. Geller, A. Gerlach, C. M. Krüger, H.-C. Militzer, J. Mol. Catal. A 2006, 251, 71.
63. A. Gerlach, T. Geller, Adv. Synth. Catal. 2004, 346, 1247.
64. H. Yi, G. Zou, Q. Li, Q. Chen, J. Tang, M.-Y. He, Tetrahedron Lett 2005, 46, 5665.
65. A. Berkessel, B. Koch, C. Toniolo, M. Rainaldi, Q. B. Broxterman, B. Kaptein, Biopolymers (Peptide Science). 2006, 84, 90.
66. W. Qiu, L. He, Q. Chen, W. Luo, Z. Yu, F. Yang, J. Tang, Tetrahedron Lett. 2009, 50, 5225.
67. R. W. Flood, T. P. Geller, S. A. Petty, S. M. Roberts, J. Skidmore, M. Volk, Org. Lett. 2001, 3, 683.
68. S. B. Tsogoeva, J. Wöltinger, C. Jost, D. Reichert, A. Kühnle, H.-P. Krimmer, K. Drauz, Synlett 2002, 707.
69. A. Berkessel, N. Gasch, K. Glaubitz, C. Koch, Org. Lett. 2001, 3, 3839.
70. D. R. Kelly, S. M. Roberts, Chem. Commun. 2004, 2018.
71. G. Carrea, S. Colonna, A. D. Meek, G. Ottolina, S. M. Roberts, Tetrahedron: Asymmetry 2004, 15, 2945.
72. S. P. Mathew, S. Gunathilagan, S. M. Roberts, D. G. Blackmond, Org. Lett. 2005, 7, 4847.
73. (a), R. Helder, J. C. Hummelen, R. W. P. M. Laane, J. S. Wiering, H. Wynberg, Tetrahedron Lett. 1976, 1831
74. (b), H. Wynberg, B. Greijdanus, J. Chem. Soc. Chem. Commun. 1978, 427
75. (c), J. C. Hummelen, H. Wynberg, Tetrahedron Lett. 1978, 1089
76. (d), H. Wynberg, B. Marsman, J. Org. Chem. 1980, 45, 158
77. (e), H. Pluim, H. Wynberg, J. Org. Chem. 1980, 45, 2498.
78. B. Lygo, P. G. Wainwright, Tetrahedron Lett. 1998, 39, 1599.
79. B. Lygo, P. G. Wainwright, Tetrahedron 1999, 55, 6289.
80. E. J. Corey, F.-Y. Zhang, Org. Lett. 1999, 1, 1287.
81. B. Lygo, D. C. M. To, Tetrahedron Lett. 2001, 42, 1343.
82. B. Lygo, S. D. Gardiner, M. C. McLeod, D. C. M. To, Org. Biomol. Chem. 2007, 5, 2283.
83. B. Lygo, D. C. M. To, Chem. Commun. 2002, 2360.
84. J. Ye, Y. Wang, R. Liu, G. Zhang, Q. Zhang, J. Chen, X. Liang,. Chem. Commun. 2003, 2714.
85. J. Ye, Y. Wang, J. Chen, X. Liang, Adv. Synth. Catal. 2004, 346, 691.
86. S. Arai, H. Tsuge, T. Shioiri, Tetrahedron Lett. 1998, 39, 7563.
87. S. Arai, H. Tsuge, M. Oku, M. Miura, T. Shioiri, Tetrahedron 2002, 58, 1623.
88. L. Alcaraz, G. Macdonald, J. P. Ragot, N. Lewis, R. J. K. Taylor, J. Org. Chem. 1998, 63, 3526.
89. S. Arai, M. Oku, M. Miura, T. Shioiri, Synlett 1998, 1201.
90. A. Berkessel, M. Guixà, F. Schmidt, J. M. Neudörfl, J. Lex, Chem. Eur. J. 2007, 13, 4483.
91. W. Adam, P. B. Rao, H.-G. Degen, A. Levai, T. Patonay, C. R. Saha-Möller, J. Org. Chem. 2002, 67, 259.
92. T. Ooi, D. Ohara, M. Tamura, K. Maruoka, J. Am. Chem. Soc. 2004, 126, 6844.
93. X. D. Liu, X. L. Bai, X. P. Qiu, L. X. Gao, Chin. Chem. Lett. 2005, 16, 975.
94. S.-S. Jew, J.-H. Lee, B.-S. Jeong, M.-S. Yoo, M.-J. Kim, Y.-J. Lee, J. Lee, S.-H. Choi, K. Lee, M. S. Lah, H.-G. Park, Angew. Chem. Int. Ed. 2005, 44, 1383.
95. J. Lv, X. Wang, J. Liu, L. Zhang, Y. Wang, Tetrahedron: Asymmetry 2006, 17, 330.
96. (a), P. Bakó, T. Bakó, A. Mészáros, G. Keglevich, Á. Szöllosy, S. Bodor, A. Makó, L. Toke, Synlett 2004, 643
97. (b), T. Bakó, P. Bakó, G. Keglevich, P. Bombicz, M. Kubinyi, K. Pál, S. Bodor, A. Makó, L. Toke, Tetrahedron: Asymmetry 2004, 15, 1589
98. (c), P. Bakó, A. Makó, G. Keglevich, M. Kubinyi, K. Pál, Tetrahedron: Asymmetry 2005, 16, 1861.
99. R. Zimmer, M. Taszarek, L. Schefzig, H.-U. Reissig, Synlett 2008, 2046.
100. A. Lattanzi, Org. Lett. 2005, 7, 2579.
101. A. Lattanzi, Adv. Synth. Catal. 2006, 348, 339.
102. A. Lattanzi, A. Russo, Tetrahedron 2006, 62, 12264.
103. A. Russo, A. Lattanzi, Eur. J. Org. Chem. 2008, 2767.
104. A. Russo, A. Lattanzi, Synthesis 2009, 1551.
105. Y. Li, X. Liu, Y. Yang, G. Zhao, J. Org. Chem. 2007, 72, 288.
106. H. Cui, Y. Li, C. Zheng, G. Zhao, S. Zhu, J. Fluorine Chem. 2008, 129, 45.
107. J. Lu, Y.-H. Xu, F. Liu, T.-P. Loh, Tetrahedron Lett. 2008, 49, 6007.
108. X. Wang, C. M. Reisinger, B. List, J. Am. Chem. Soc. 2008, 130, 6070.
109. M. Marigo, J. Franzén, T. B. Poulsen, W. Zhuang, K. A. JAørgensen, J. Am. Chem. Soc. 2005, 127, 6964.
110. W. Zhuang, M. Marigo, K. A. JAørgensen, Org. Biomol. Chem. 2005, 3, 3883.
111. H. Sundén, I. Ibrahem, A. Córdova, Tetrahedron Lett. 2006, 47, 99.
112. G.-L. Zhao, I. Ibrahem, H. Sundén, A. Córdova, Adv. Synth. Catal. 2007, 349, 1210.
113. S. Lee, D. W. C. MacMillan, Tetrahedron 2006, 62, 11413.
114. X. Wang, B. List, Angew. Chem. Int. Ed. 2008, 47, 1119.
115. T. Ishikawa, T. Isobe, Chem. Eur. J. 2002, 8, 552.
116. M. T. Allingham, A. Howard-Jones, P. J. Murphy, D. A. Thomas, P. W. R. Caulkett, Tetrahedron Lett 2003, 44, 8677.
117. M. Terada, H. Ube, S. Yokoyama, H. Shimizu, Patent US 2008 / 0154036 A1.
118. J. C. McManus, T. Genski, J. S. Carey, R. J. K. Taylor, Synlett 2003, 369.
119. J. C. McManus, J. S. Carey, R. J. K. Taylor, Synlett 2003, 365.
120. S. Tanaka, K. Nagasawa, Synlett 2009, 667.
121. W. Adam, P. B. Rao, H.-G. Degen, C. R. Saha-Möller, J. Am. Chem. Soc. 2000, 122, 5654.
122. A. Lattanzi, M. Cocilova, P. Iannece, A. Scettri, Tetrahedron: Asymmetry 2004, 15, 3751.
123. A. Bundu, N. G. Berry, C. D. Gill, C. L. Dwyer, A. V. Stachulski, R. J. K. Taylor, J. Whittall, Tetrahedron: Asymmetry 2005, 16, 283.
124. W. Kośnik, A. V. Stachulski, M. Chmielewski, Tetrahedron: Asymmetry, 2005, 16, 1975.
125. W. Kośnik, W. Bocian, L. Kozerski, I. Tvaroška, M. Chmielewski, Chem. Eur. J. 2008, 14, 6087.
126. K. Oh, J. Ryu, Tetrahedron Lett. 2008, 49, 1935.