Phenylselenoethers as precursors of acyclic free radicals. Creating tertiary and quaternary centers using free radical-based intermediates

Current Organic Chemistry

Volumn 10, Issue 15, 2006, Pages 1939-1961

  Cardinal David, Benoit ^a,b,c   Brazeau, Jean François ^a,b,c   Katsoulis, Ioannis A ^a,b,c   Guindon, Yvan ^a,b,c  

^a CLIN RESEARCH INSTITUTE OF MONTREAL   (Canada)

^b UNIVERSITÉ DE MONTRÉAL   (Canada)

^c MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; ALKENE; BETA BENZYLOXYALDEHYDE; BROMOENOXYSILANE; CARBON; CARBONYL DERIVATIVE; ESTER DERIVATIVE; FREE RADICAL; HALIDE; HYDROXYL GROUP; LEWIS ACID; ORGANOSELENIUM DERIVATIVE; PHENYLSELENOENOXYSILANE DERIVATIVE; PHENYLSELENOETHER DERIVATIVE; PROPIONIC ACID DERIVATIVE; SELENIUM; SELENIUM DERIVATIVE; SELENOESTER DERIVATIVE; SILANE DERIVATIVE; TITANIUM TETRACHLORIDE; UNCLASSIFIED DRUG;

ADDITION REACTION; ALDOL REACTION; ALLYLATION; CARBON NUCLEAR MAGNETIC RESONANCE; CHELATION; CHEMICAL BOND; CHEMICAL INTERACTION; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CHIRALITY; COMPLEX FORMATION; COVALENT BOND; CYCLIZATION; DECOMPOSITION; DIPOLE; ENANTIOSELECTIVITY; POLYMERIZATION; PROTON TRANSPORT; REVIEW; STEREOCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS; THERMODYNAMICS;

EID: 33749429609     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527206778521259     Document Type: Review

References (132)

1. For excellent reviews and monographs: (a) Porter, N. A.; Giese, B.; Curan, D. P. Acc. Chem. Res. 1991, 24, 296.
2. (b) Smadja, W. Synlett 1994, 6, 1.
3. (c) Sibi, M. P.; Porter, N. A. Acc. Chem. Res. 1999, 32, 163.
4. (d) Sibi, M. P.; Manyem, S.; Zimmerman, J. Chem. Rev. 2003, 103, 3263.
5. (e) Bar, G.; Parsons, A. F. Chem. Soc. Rev. 2003, 32, 251.
6. (f) Curran, D. P. Comprehensive Organic Synthesis; Semmelhack, M. F., Ed.; Pergamon Press: Oxford, U.K., 1991.
7. (g) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions, VCH: Weinheim, 1995.
8. (h) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions-Concepts, Guidelines and Synthetic Applications; VCH: New York, 1996.
9. (a) Porter, N. A.; Scott, D. M.; Lacher, B.; Giese, B.; Zeitz, H.-G; Linder, H. J. J. Am. Chem. Soc. 1989, 111, 8311.
10. (b) Curran, D. P.; Shen, W.; Zhang, J.; Heffner, T. A. J. Am. Chem. Soc. 1990, 112, 6738.
11. (c) Porter, N. A. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 1, Chapter 4.3.
12. See for early reviews: (a) Hart, D. J.; Huang, H.-C. Tetrahedron Lett. 1985, 26, 3749.
13. (b) Giese, B.; Zehnder, M.; Roth, M.; Zeitz, H. G. J. Am. Chem. Soc. 1990, 112, 6741.
14. (c) Hart, D. J.; Krishnamurthy, R. J. Org. Chem. 1992, 57, 4457.
15. (d) Giese, B.; Damm, W.; Wetterich, F.; Zeitz, H.-G. Tetrahedron Lett. 1992, 33, 1863.
16. Guindon, Y.; Yoakim, C.; Lemieux, R.; Boisvert, L.; Delorme, D.; Lavallée, J. F. Tetrahedron Lett. 1990, 31, 2845.
17. Renaud, P.; Gerster, M. Angew. Chem. Int. Ed. 1998, 37, 2563.
18. Guindon, Y.; Lavallée, J.-F.; Llinas-Brunet, M.; Horner, G.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 9701.
19. (a) Urabe, H.; Yamashita, K.; Suzuki, K.; Kobayashi, K.; Sato, F. J. Org. Chem. 1995, 60, 3576.
20. (b) Porter, N. A.; Wu, J. H.; Zhang, G.; Reed, A. D. J. Org. Chem. 1997, 62, 6702.
21. (c) Murakata, M.; Tsutsui, H.; Takeuchi, N.; Hoshino, O. Tetrahedron 1999, 55, 10295.
22. (d) Sibi, M. P.; Asano, Y.; Sausker, J. B. Angew. Chem. Int. Ed. 2001, 40, 1293.
23. Guérin, B.; Ogilvie, W. W.; Guindon, Y. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 1, Chapter 4.4.
24. Renaud, P. Top. Curr. Chem. 2000, 208, 81.
25. Guindon, Y.; Houde, K.; Prévost, M.; Cardinal-David, B.; Landry, S. R.; Daoust, B.; Bencheqroun, M.; Guéin, B. J. Am. Chem. Soc. 2001, 123, 8496.
26. Guindon, Y.; Prévost, M.; Mochirian, P.; Guérin, B. Org. Lett. 2002, 4, 1019.
27. Mochirian, P.; Cardinal-David, B.; Guérin, B.; Prévost, M., Guindon, Y. Tetrahedron Lett. 2002, 43, 7067.
28. Guindon, Y.; Brazeau, J.-F. Org. Lett. 2004, 6, 2599.
29. Cardinal-David, B.; Guérin, B.; Guindon, Y. J. Org. Chem. 2005, 70, 776.
30. For excellent reviews on the synthesis of quartenary centers see: (a) Marlin, S. F. Tetrahedron 1980, 36, 419.
31. (b) Fuji, K. Chem. Rev. 1993, 93, 2037.
32. (c) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388.
33. (d) Christoffers, J.; Mann, A. Angew. Chem. Int. Ed. Engl. 2001, 40, 4591.
34. (e) Denissova, I.; Barriault, L. Tetrahedron 2003, 59, 10105.
35. Marshall, J. A.; Perkins, J. F.; Wolf, M. A. J. Org. Chem. 1995, 60, 5556.
36. (a) Griller, D.; Cooper, J. W.; Ingold, K. U. J. Am. Chem. Soc. 1975, 97, 4269.
37. (b) Hart, D. J.; Huang, H.-C.; Krishnamurthy, R.; Schwartz, T. J. Am. Chem. Soc. 1989, 111, 7507-7519.
38. (c) Giese, B.; Bulliard, M.; Zeitz, H.,-G. Synlett 1991, 6, 425-427.
39. (d) Mile, B. Curr. Org. Chem. 2000, 4, 55.
40. Porter, N. A. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 1, Chapter 4.3.
41. Porter, N. A.; Wu, W.-X.; McPhail, A. T. Tetrahedron Lett. 1991, 32, 707.
42. (a) Hart, D.J; Huang, H. C; Krishnamurthy, R.; Schwartz, T. J. Am. Chem. Soc. 1989, 111, 7507.
43. (b) Giese, B.; Bulliard, M.; Zeitz, H.-G. Synlett 1991, 425.
44. Guindon, Y.; Slassi, A.; Rancourt, J.; Bantle, G.; Bencheqroun, M.; Murtagh, L.; Ghiro, É.; Jung, G. J. Org. Chem. 1995, 60, 288.
45. Durkin, K.; Liotta, D.; Rancourt, J.; Lavalée, J.-F.; Boisvert, L.; Guindon, Y. J. Am. Chem. Soc. 1992, 114, 4912.
46. Giese, B.; Damm, W.; Wetterich, F.; Zeitz, H.-G.; Rancourt, J.; Guindon, Y. Tetrahedron Lett. 1993, 34, 5885.
47. Guindon, Y.; Jung, G.; Guérin, B.; Ogilvie, W. W. Synlett 1998, 3, 213.
48. Guindon, Y.; Guérin, B.; Rancourt, J.; Chabot, C.; Mackintosh, N.; Ogilvie, W. W. Pure Appl. Chem 1996, 68, 89.
49. Guérin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W. W.; Guindon, Y. Can. J. Chem. 2000, 78, 852.
50. Guindon, Y.; Guérin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W. W. Synlett 1995, 5, 449.
51. Guindon, Y.; Faucher, A.-M.; Bourque, É.; Caron, V.; Jung, G.; Landry, S. R. J. Org. Chem. 1997, 62, 9276.
52. Bouvier, J.-P.; Jung, G.; Liu, Z.; Guérin, B.; Guindon, Y. Org. Lett. 2001, 3, 1391.
53. Guindon, Y.; Liu, Z.; Jung, G. J. Am. Chem. Soc. 1997, 119, 9289.
54. (a) Imoto, M.; Otsu, T.; Harada, Y. Makromol. Chem. 1963, 65, 180.
55. (b) Kuivila, H. G.; Menapace, L. W. J. Org. Chem. 1963, 28, 2165.
56. (c) Kuivila, H. G. Adv. Organomet. Chem. 1964, 1, 47.
57. (d) Menapace, L. W.; Kuivila, H. G. J. Am. Chem. Soc. 1964, 86, 3047.
58. (e) Yabumoto, S.; Ishii, K.; Arita, K. J. Polym. Sci. A-1, 1969, 7, 1577.
59. (f) Kuivila, H. G. Synthesis 1970, 499.
60. (g) Inoue, H.; Otsu, T. Makromol. Chem. 1972, 153, 21.
61. (a) Renaud, P. Ribezzo, M. J. Am. Chem. Soc. 1991, 113, 7803.
62. (b) Renaud, P.; Moufid, N.; Kuo, L. H.; Curran, D. P. J. Org. Chem. 1994, 59, 3547.
63. For hydrogen transfer reactions, the syn or anti diastereoselectivity is determined by looking at the C2 methyl and the C3 hydroxyl. For allylation reactions, it is determined by looking at the C2 allyl and the C3 hydroxyl.
64. The ligands on L.A. have been excluded for simplicity.
65. Giese, B. Angew. Chem. Int. Ed. Engl. 1983, 22, 753.
66. Silyl ethers are known to be less efficient in complexation with Lewis acids. See Chen, X.; Hortelano, E. R.; Eliel, E. L.; Frye, S. V. J. Am. Chem. Soc. 1992, 114, 1778 and references therein.
67. For reviews see: (a) Curran, D. P. Synthesis 1988, 489.
68. (b) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237.
69. (a) Curran, D. P.; Bosch, E.; Kaplan, J.; Newcomb, M. J. Org. Chem. 1989, 54, 1826.
70. (b) Curran, D. P.; Chen, M.-H.; Spletzer, E.; Seong, C. M.; Chang, C.-T. J. Am. Chem. Soc. 1989, 111, 8872.
71. (c) Curran, D. P.; Chang, C.-T. J. Org. Chem. 1989, 54, 3140.
72. Curran, D. P.; Seong, C. M. Tetrahedron 1992, 48, 2157.
73. (b) Curran, D. P.; Seong, C. M. J. Am. Soc. 1990, 112, 9401.
74. Back, T. G.; Gladstone, P. L. Synlett 1993, 699.
75. (b) Back, T. G.; Gladstone, P. L.; Parvez, M. J. Org. Chem. 1996, 61, 3806.
76. (a) Mero, C. L.; Porter, N. A. J. Am. Chem. Soc. 1999, 121, 5155.
77. (b) Porter, N. A.; Wu, J. H.; Zhang, G.; Reed, A. D. J. Org. Chem. 1997, 62, 6702.
78. (c) Porter, N. A.; Zhang, G.; Reed, A. D. Tetrahedron Lett. 2000, 41, 5773.
79. (d) Feng, H.; Kavrakova, I. K.; Pratt, D. A.; Tellinghuisen, J.; Porter, N. A. J. Org. Chem. 2002, 67, 6050.
80. (e) Yang, D.; Yan, Y.-L.; Law, K.-L.; Zhu, N.-Y. Tetrahedron 2003, 59, 10465.
81. For other tin-free radical allylation methods: (a) Le Guyader, F.; Quiclet-Sire, B.; Seguin, S.; Zard, S. Z. J. Am. Chem. Soc. 1997, 119, 7410.
82. (b) Usugi, S.-i.; Yorimitsu, H.; Oshima, K. Tetrahedron Lett. 2001, 42, 4535 and references therein.
83. (c) Schaffner, A.-P.; Renaud, P. Angew. Chem. Int. Ed. 2003, 42, 2658.
84. For other examples of radical-based allylation reactions with allyltrimethylsilane, see: (a) Saito, I.; Ikehira, H.; Matsuura, T. Tetrahedron Lett. 1985, 26, 1993.
85. (b) Hirao, T.; Fujii, T.; Ohshiro, Y. Tetrahedron Lett. 1994, 35, 8005.
86. (c) Hwu, J. R.; Chen, C. N.; Shiao, S.-S. J. Org. Chem. 1995, 60, 856.
87. (d) Porter, N. A.; Wu, J. H.; Zhang, G.; Reed, A. D. J. Org. Chem. 1997, 62, 6702.
88. (e) Hwu, J. R.; King, K. Y.; Wu, I.-F.; Hakimelahi, G. H. Tetrahedron Lett. 1998, 39, 3721.
89. For other allylsilane-based reagents, see: (a) Chatgilialoglu, C.; Ballestri, M.; Vecchi, D.; Curran, D. P. Tetrahedron Lett. 1996, 37, 6383.
90. (b) Chatgilialoglu, C.; Ferreri, C.; Ballestri, M.; Curran, D. P. Tetrahedron Lett. 1996, 37, 6387.
91. In comparison, selenium transfer is a rather slow process. See: (a) Schiesser, C. H.; Wild, L. M. Tetrahedron 1996, 52, 13265.
92. (b) Curran, D. P.; Martin-Esker, A. A.; Ko, S. B.; Newcomb, M. J. Org. Chem. 1993, 58, 4691.
93. For an interesting example of hydrogen-bonding as a stereocontrolling element in free radical-based allylation reactions, see: Hanessian, S.; Yang, H.; Schaum, R. J. Am. Chem. Soc. 1996, 118, 2507.
94. Normally, a 2/1 (syn/anti) selectivity is obtained from β-hydroxyesters.
95. Other methodologies for the synthesis of such molecules have been developed: Frater's anionic alkylation: (a) Fráter, G. Helv. Chim. Acta 1979, 62, 2825.
96. (b) Fráter, G.; Müller, U.; Günther, W. Tetrahedron 1984, 40, 1269. Aldol-based strategies:
97. (c) Manthorpe, J. M.; Gleason, J. L. J. Am. Chem. Soc. 2001, 123, 2091.
98. (d) Burke, E. D.; Gleason, J. L. Org. Lett. 2004, 6, 405. Addition of allylmetals to aldehydes:
99. (e) Kennedy, J. W. J.; Hall, D. G. J. Am. Chem. Soc. 2002, 124, 898.
100. (f) Kennedy, J. W. J.; Hall, D. G. J. Am. Chem. Soc. 2002, 124, 11586.
101. (g) Sklute, G.; Amsallem, D.; Shabli, A.; Varghese, J. P.; Marek, I. J. Am. Chem. Soc. 2003, 125, 11776. Allylmetal opening of chiral epoxides:
102. (h) Ohno, H.; Hiramatsu, K.; Tanaka, T. Tetrahedron Lett. 2004, 45, 75.
103. 3Al: Gerster, M.; Audergon, L.; Moufid, N.; Renaud, P. Tetrahedron Lett. 1996, 37, 6335.
104. For other examples showing the influence of the stereochemistry of the radical precursor, see: a) Ishihara, T.; Mima, K.; Konno, T.; Yamanaka, H. Tetrahedron Lett. 2002, 43, 3493.
105. (b) Sibi, M. P.; Rhesult, T. R. J. Am. Chem. Soc. 2000, 122, 8873.
106. Chen, X.; Hortelano, E. R.; Eliel, E. L.; Frye, S. V. J. Am. Chem. Soc. 1992, 114, 1778.
107. Hoffmann, R. W. Angew. Chem. Int. Ed. Eng. 1987, 26, 489.
108. Zincophorin: Komatsu, K.; Tanino, K.; Miyashita, M. Angew. Chem., Int. Ed. Eng. 2004, 43, 4341 and references therein.
109. Tolytoxin: See the interesting review on marine macrolides by Young, K.-S.; Paterson, I. Angew. Chem. Int. Ed. 2002, 41, 4632.
110. (a) Selected examples: (a) Evans, D. A.; Ng, H. P.; Clark, J. S.; Rieger, D. L. Tetrahedron 1992, 48, 2127.
111. (b) Chemler, S. R.; Roush, W. R. J. Org. Chem. 1998, 63, 3800.
112. (c) Panek, J. S.; Jain, N. F. J. Org. Chem. 1998, 63, 4572
113. (d) Hanessian, S.; Ma, J.; Wang, W. Tetrahedron Lett. 1999, 40, 4627.
114. (e) Paterson, I.; Chen, D. Y. K.; Acena, J. L.; Franklin, A. S. Org. Lett. 2000, 2, 1513.
115. (f) Marshall, J. A.; Schaaf, G. M. J. Org. Chem. 2001, 66, 7825.
116. (a) Mukaiyama, T.; Banno, K.; Narasaka, K. J. Am. Chem. Soc. 1974, 96, 7503.
117. (b) Gennari, C. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1993; Vol. 2, Chapter 2.4, p 629.
118. (a) Eliel, E. L. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1983; Vol. 2, Chapter 5, pp. 125.
119. (b) Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1984, 23, 556.
120. (c) Reetz, M. T.; Hüllmann, M.; Seitz, T. Angew. Chem., Int. Ed. Engl. 1987, 26, 477.
121. Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 9, 2199.
122. (b) Anh, N. T.; Eisenstein, O. Nouv. J. Chim. 1977, 1, 61.
123. (c) Anh, N. T. Top. Curr. Chem. 1980, 88, 145.
124. One should note that hydrogen transfer reactions involving 2,3-syn or 2,3-anti phenylselenoethers and bromides were shown to be diastereoselective even when syn precursors were used.
125. (a) Evans, D.A.; Allison, B. D.; Yang, M.G.; Masse, C. E. J. Am. Chem. Soc. 2001, 123, 10840.
126. (b) Evans, D. A.; Dart, M. J.; Duffy, J. L.; Yang, M. G. J. Am. Chem. Soc. 1996, 118, 4322.
127. 4-promoted Mukaiyama reactions. Bernardi, A.; Cardani, S.; Colombo, L.; Poli, G.; Schimperna, G.; Scolastico, C. J. Org. Chem. 1987, 52, 888.
128. Koster, R.; Fenzl, W.; Seidel, G. Liebigs Ann. Chem. 1975, 352.
129. Kiyooka, S.-I. Tetrahedron Asymmetry 2003, 14, 2897 and reference therein.
130. Guindon, Y.; Murtagh, L.; Caron, V.; Landry, S. R.; Jung, G.; Bencheqroun, M.; Faucher, A.-M.; Guérin, B. J. Org. Chem. 2001, 66, 5427.
131. Lee, E.; Choi, S. J. Org. Lett. 1999, 1, 1127.
132. Jeong, E. J.; Kang, E. J.; Sung, L. T.; Hong, S. K.; Lee, E. J. Am. Chem. Soc. 2002, 124, 14655.