γ-Silylated α,ß-unsaturated amides - Preparation by [1,5]-sigmatropic rearrangement and use as masked dienolate equivalents in carbonyl condensations

Canadian Journal of Chemistry

Volumn 87, Issue 6, 2009, Pages 745-759

  Green, James R ^a   Alo, Babajide I ^b   Majewski, Marek ^c   Snieckus, Victor ^d,e  

^a UNIVERSITY OF WINDSOR   (Canada)

^b UNIVERSITY OF LAGOS   (Nigeria)

^c UNIVERSITY OF SASKATCHEWAN   (Canada)

^d UNIVERSITY OF WATERLOO   (Canada)

^e QUEEN S UNIVERSITY   (Canada)

Author keywords

Allylsilane; Amide dienolate; Hosomi Sakurai reaction; Silicon migration; Stereoselective

Indexed keywords

[CARBONYL; ALLYLSILANE; AROMATIC ALDEHYDE; BIDENTATE COORDINATION; CONDENSATION PRODUCT; ELECTROPHILES; HOSOMI-SAKURAI REACTION; MEDIATED REACTIONS; OXYGEN ATOM; SIGMATROPIC REARRANGEMENTS; STEREOSELECTIVE; TRANSITION STATE; UNSATURATED AMIDES;

ALDEHYDES; AMIDES; CONDENSATION; LITHIUM; OXYGEN; SILANES; STEREOSELECTIVITY; TITANIUM;

COORDINATION REACTIONS;

EID: 67650318506     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/V09-054     Document Type: Article

References (100)

1. Dedicated to Peter Beak, in recognition of a career of rigorous physical organic studies, which enduringly enriched the field of carbanionic chemistry.
2. Casiraghi, G.; Zanardi, F.; Appendino, G.; Rassu, G. Chem. Rev. 2000, 100, 1929 doi:10.1021/cr990247i. PMID: 11749280
3. Denmark, S. E.; Heemstra, J. R., Jr.; Beutner, G. L. Angew. Chem., Int. Ed. 2005, 44, 4682 doi:10.1002/anie.200462338
4. Green, J. R. In Science of synthesis; Majewski, M. and Snieckus, V., Eds; Georg Thieme Verlag: Stuttgart, 2006; Vol.8, pp. 427-486
5. Casinos, I.; Mestres, R. J. Chem. Soc., Perkin Trans 1978, 1, 1651 doi:10.1039/p19780001651
6. Dugger, R. W.; Heathcock, C. H. J. Org. Chem. 1980, 45, 1181. doi:10.1021/jo01295a002.
7. Majewski, M.; Mpango, G. B.; Thomas, M. T.; Wu, A.; Snieckus, V. J. Org. Chem. 1981, 46, 2029 doi:10.1021/jo00323a012
8. Majewski, M.; Green, J. R.; Snieckus, V. Tetrahedron Lett. 1986, 27, 531 doi:10.1016/S0040-4039(00) 84032-0
9. Green, J. R.; Majewski, M.; Snieckus, V. Can. J. Chem. 2006, 84, 1397. doi:10.1139/V06-112.
10. Casey, C. P.; Jones, C. R.; Tukada, H. J. Org. Chem. 1981, 46, 2089. doi:10.1021/jo00323a022.
11. For reviews on ketene acetals, see: Schneider, C. In Science of synthesis; de Meijere, A., Ed.; Georg Thieme Verlag: Stuttgart, 2005; Vol.24, pp. 293-322
12. Mahrwald, R. Chem. Rev. 1999, 99, 1095 doi:10.1021/cr980415r. PMID:11749441
13. For a review on ketene O,N-acetals, see: Kantlehner, W. In Science of synthesis; de Meijere, A., Ed.; Georg Thieme Verlag: Stuttgart, 2005; Vol.24, pp. 337-446
14. For reviews on the chemistry of vinyl ketene acetals, see: Kalesse, M. Top. Curr. Chem. 2005, 244, 43
15. Casiraghi, G.; Zanardi, F.; Appendino, G.; Rassu, G. Chem. Rev. 2000, 100, 1929. doi:10.1021/cr990247i. PMID: 11749280.
16. Williard, P. G.; Tata, J. R.; Schlessinger, R. H.; Adams, A. D.; Iwanowicz, E. J. J. Am. Chem. Soc. 1988, 110, 7901. doi:10.1021/ja00231a065.
17. In esters, see: Kang, G. J.; Chan, T. H. Can. J. Chem. 1985, 63, 3102 doi:10.1139/v85-512
18. Barton, T. J.; Goure, W. F.; Witiak, J. L.; Wulff, W. D. J. Organomet. Chem. 1982, 225, 87 doi:10.1016/S0022-328X(00)86813-8.;
19. Bellassoued, M.; Ennigrou, R.; Gaudemar, M. J. Organomet. Chem. 1988, 338, 149 doi:10.1016/0022-328X(88) 80497-2
20. Asakura, T.; Kojima, T.; Miura, T.; Iwasawa, N. Angew. Chem., Int. Ed. 2006, 45, 6874. doi:10.1002/anie. 200602188.
21. In ketones and aldehydes, see: Shih, C.; Swenton, J. S. J. Org. Chem. 1982, 47, 2668 doi:10.1021/jo00134a032.
22. Fish, P. V. Synth. Commun. 1996, 26, 433 doi:10.1080/00397919608003634.
23. Bartoli, G.; Bosco, M.; Dalpozzo, R.; De Nino, A.; Iantorno, E.; Tagarelli, A.; Palmieri, G. Tetrahedron 1996, 52, 9179 doi:10.1016/0040-4020(96) 00468-1
24. Pirrung, M. C.; Fallon, L.; Zhu, J.; Lee, Y. R. J. Am. Chem. Soc. 2001, 123, 3638 doi:10.1021/ja002370t. PMID:11457095
25. Asakura, T.; Kojima, T.; Miura, T.; Iwasawa, N. Angew. Chem., Int. Ed. 2006, 45, 6874. doi:10. 1002/anie.200602188.
26. For a review of silicon migrations, see: Mitsuo, K.; Iwamoto, T. In Chemistry of organic silicon compounds; Rappoport, Z., Apeloig, Y., Eds.; Wiley: Chichester, 2001; Vol.3, pp. 853-948.
27. For the preliminary report, see: Green, J. R.; Snieckus, V. Tetrahedron Lett. 1986, 27, 535. doi:10.1016/S0040-4039(00)84033-2
28. Armstrong, R. J.; Weiler, L. Can. J. Chem. 1983, 61, 2530 doi:10.1139/v83-436
29. Pettersson, L.; Magnuson, G.; Frejd, T. Acta Chem. Scand. 1993, 47, 196 doi:10.3891/acta.chem.scand.47-0196
30. Wennerberg, J.; Polla, M.; Frejd, T. J. Org. Chem. 1997, 62, 8735 doi:10.1021/jo971082l
31. Nakada, M.; Kojima, E.-i.; Iwata, Y. Tetrahedron Lett. 1998, 39, 313 doi:10.1016/S0040-4039(97)10554-8
32. Aggarwal, V. K.; Bethel, P. A.; Giles, R. J. Chem. Soc., Perkin Trans 1999, 1, 3315 doi:10.1039/a906589j.
33. Beszant, S.; Giannini, E.; Zanoni, G.; Vidari, G. Tetrahedron Asymmetry 2002, 13, 1245 doi:10.1016/S0957-4166(02) 00335-X.
34. Pettersson, L.; Frejd, T. J. Chem. Soc., Perkin Trans. 2001, 1, 789 doi:10.1039/b010101j.
35. Beszant, S.; Giannini, E.; Zononi, G.; Vidari, G. Eur. J. Org. Chem. 2003, 3958. doi:10.1002/ejoc.200300276.
36. For broader study of electrophilic reactivity with alkenoates, see: Yamamoto, Y.; Hatsuya, S.; Yamada, J.-i. J. Org. Chem. 1990, 55, 3118 doi:10.1021/jo00297a030.
37. Fan, R.; Hudlicky, T. Tetrahedron Lett. 1989, 30, 5533 doi:10. 1016/S0040-4039(01)93792-X.
38. For amination reactions, see: Loreto, M. A.; Pompei, F.; Tardella, P. A.; Tofavi, D. Tetrahedron 1997, 53, 15853. doi:10.1016/S0040-4020(97) 10045-X.
39. Chabaud, L.; James, P.; Landais, Y. Eur. J. Org. Chem. 2004, 3173 doi:10.1002/ejoc.200300789.
40. Sarkar, T. K. In Science of synthesis; Fleming, I., Ed.; Georg Thieme Verlag: Stuttgart, 2002; Vol.4, pp. 837-926
41. Brook, M. A. Silicon in organic, organometallic, and polymer chemistry; Wiley: New York, 2000; Chap. 16
42. Luh, T.-Y.; Liu, S.-T. In Chemistry of organic silicon compounds; Rappoport, Z., Apeloig, Y., Eds.; Wiley: Chichester, 1998; Vol.2, Pt. 3, pp. 1793-1868
43. Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063 doi:10.1021/cr941074u. PMID: 11848898.
44. Langkopf, E.; Schinzer, D. Chem. Rev. 1995, 95, 1375 doi:10.1021/ cr00037a011.
45. Fleming, I.; Dunogues, J.; Smithers, R. Org. React. 1989, 37, 57
46. Majetich, G. In Organic synthesis: theory and applications; Hudlicky, T, Ed.; JAI: Greenwich, 1989; Vol.1, pp. 173-240.
47. Denmark, S. E.; Lee, W. Chem. Asian J. 2008, 3, 327 doi:10.1002/asia. 200700300. PMID:18022982.
48. Kalese, M.; Hassfeld, J. In Asymmetric synthesis: the essentials; Christmann, M., Bräse, S., Eds.; Wiley-VCH: Weinheim, 2007; pp. 105-109
49. Hosokawa, S.; Tatsuta, K. Mini Rev. Org. Chem. 2008, 5, 1 doi:10.2174/157019308783498197.;
50. Jacques, T.; Markó, I. E.; Popisil, J. In Multicomponent reactions; Zhu, J, Bienaymé, H., Eds.; Wiley-VCH, 2005; pp. 398-452.
51. For an analogous NOE-based assignment of the alkene stereochemistry of vinylketene acetals, see: Bell, S. H.; Cameron, D. W.; Feutrill, G. I.; Skelton, B. W.; White, A. H. Tetrahedron Lett. 1985, 26, 6519 doi:10.1016/S0040- 4039(00)99042-99047
52. Adams, A. D.; Schlessinger, R. H.; Tata, J. R.; Venit, J. J. J. Org. Chem. 1986, 51, 3068. doi:10. 1021/jo00365a045.
53. Berger, S.; Braun, S. 200 and more NMR experiments: A practical course, Wiley-VCH: Weinheim, 2004; pp. 277- 279.
54. For examples of the influence of phenyl groups in silyl halides on O- versus C-silylation, see: Larson, G. L.; Fuentes, L. M. J. Am. Chem. Soc. 1981, 103, 2418 doi:10.1021/ja00399a052.
55. Akai, S.; Kitagaki, S.; Naka, T.; Yamamoto, K.; Tsuzuki, Y.; Matsumoto, K.; Kita, Y. J. Chem. Soc., Perkin Trans. 1996, 1, 1705. doi:10.1039/ p19960001705.
56. House, H. O.; Crumrine, D.; Teranishi, A. Y.; Olmstead, H. D. J. Am. Chem. Soc. 1973, 95, 3310 doi:10.1021/ ja00791a039.
57. Heathcock, C. In Asymmetric synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1983; Vol.3, pp. 111-212.
58. For support of an ion-paired enolate intermediate, see: Biddle, M. M.; Reich, H. J. J. Org. Chem. 2006, 71, 4031 doi:10.1021/jo0522409. PMID:16709041.
59. For examples of results strongly implicating a pentacoordinated siliconate ion in a similar pKa range, see: Takahashi, O.; Maeda, T.; Mikami, K.; Nakai, T. Chem. Lett. 1986, 1355. doi:10.1246/cl.1986.1355.
60. Reetz, M.; Peter, R. Tetrahedron Lett. 1981, 22, 4691 doi:10.1016/S0040-4039(01)83014-8
61. Evans, D. A.; Urpi, F.; Somers, T. C.; Clark, J. S.; Bilodeau, M. T. J. Am. Chem. Soc. 1990, 112, 8215 doi:10.1021/ja00178a082.
62. Ghosh, A. K.; Shevlin, M. In Modern aldol reactions; Mahrwald, R., Ed.; Wiley-VCH: Weinhein, 2004; pp. 60-125.
63. Yamamoto, Y.; Hatsuya, S.; Yamada, J.-i. J. Org. Chem. 1990, 55, 3118. doi:10.1021/jo00297a030.
64. Fan, R.; Hudlicky, T. Tetrahedron Lett. 1989, 30, 5533. doi:10.1016/S0040-4039(01)93792-X.
65. Kaur, P.; Singh, P.; Kumar, S. Tetrahedron 2005, 61, 8231 doi:10.1016/j.tet.2005.06.045.
66. Hansen, F. G.; Bundgaard, E.; Madsen, R. J. Org. Chem. 2005, 70, 10139. doi:10.1021/jo051645q. PMID:16292857.
67. We and Hudlicky have chosen to define diastereomer nomenclature by the more conventional consideration of the carbonyl function as part of the main chain. Consequently, the syn- and anti-diastereomers of our work correspond to the anti- and syn-diastereomers, respectively, of theYamamoto and Kumar reports.
68. Yamamoto, Y.; Yitagai, Y.; Naruta, Y.; Maruyama, K. J. Am. Chem. Soc. 1980, 102, 7107 doi:10.1021/ja00543a040.;
69. For a more complete discussion of the possible open transition states in Hosomi-Sakurai reactions, see: Tietze, L. F.; Kinzel, T.; Schmatz, S. J. Am. Chem. Soc. 2006, 128, 11483 doi:10.1021/ja062528v. PMID:16939272.
70. For a review on diastereoselection in Mukaiyama aldol reactions, see: Mahrwald, R. Chem. Rev. 1999, 99, 1095. doi:10.1021/ cr980415r. PMID:11749441.
71. Maria, P.-C.; Gal, J.-F. J. Phys. Chem. 1985, 89, 1296. doi:10.1021/j100253a048.
72. Montaudo, G.; Librando, V.; Caccamese, S.; Maravigna, P. J. Am. Chem. Soc. 1973, 95, 6365 doi:10.1021/ ja00800a033.
73. Kruk, C.; Spaargaren, K. Spectrochim. Acta [A] 1971, 27, 77.
74. For synclinal transition-state proposals in allylsilane carbonyl condensations, cyclic, see: Denmark, S. E.; Weber, E. J. Helv. Chim. Acta 1983, 66, 1655 doi:10.1002/hlca.19830660604
75. For acyclic, see: Jain, N. F.; Takenaka, N.; Panek, J. S. J. Am. Chem. Soc. 1996, 118, 12475 doi:10. 1021/ja962877x
76. For allylstannanes, cyclic, see: Denmark, S. E.; Weber, E. J. J. Am. Chem. Soc. 1984, 106, 7970 doi:10.1021/ja00337a053
77. For allylstannanes, acyclic, see: Keck, G. E.; Savin, K. A.; Cressman, E. N. K.; Abbott, D. E. J. Org. Chem. 1994, 59, 7889. doi:10.1021/jo00104a054.
78. Evans, D. A.; Sjogren, E. B.; Bartroli, J.; Dow, R. L. Tetrahedron Lett. 1986, 27, 4957 doi:10.1016/S0040-4039(00) 85106-85110
79. Galatsis, P.; Millan, S. D.; Ferguson, G. J. Org. Chem. 1997, 62, 5048. doi:10.1021/jo961904z.
80. Moreau, B.; Ginisty, M.; Alberico, D.; Charette, A. B. J. Org. Chem. 2007, 72, 1235. doi:10.1021/jo062099j. PMID: 17256906.
81. Gevorgyan, V.; Kadota, I.; Yamamoto, Y. Tetrahedron Lett. 1993, 34, 1313 doi:10.1016/S0040-4039(00)91783-0.
82. Nishigaichi, Y.; Takuwa, A. Tetrahedron Lett. 2002, 43, 3045 doi:10.1016/S0040-4039(02)00409-414
83. Nishigaichi, Y.; Takuwa, A. Tetrahedron Lett. 2003, 44, 1405. doi:10.1016/S0040-4039(02)02867-8.
84. Goasdoue, G.; Goasdoue, N.; Gaudemar, M. J. Organomet. Chem. 1984, 263, 273 doi:10.1016/0022-328X(84)85032-9
85. Chan, T. H.; Aida, T.; Lau, P. W. K.; Gorys, V.; Harpp, D. N. Tetrahedron Lett. 1979, 4029 doi:10.1016/S0040-4039(01)86495-9
86. Schinzer, D.; Solyom, S.; Becker, M. Tetrahedron Lett. 1985, 26, 1831. doi:10.1016/S0040-4039(00)94749-X
87. Bottoni, A.; Costa, A. L.; Di Tommaso, D.; Rossi, I.; Tagliavini, E. J. Am. Chem. Soc. 1997, 119, 12131. doi:10.1021/ja9723693.
88. Denmark, S. E.; Almstead, N. G. J. Org. Chem. 1994, 59, 5130 doi:10.1021/jo00097a008.
89. Denmark, S. E.; Hosoi, S. J. Org. Chem. 1994, 59, 5133 doi:10.1021/jo00097a009.
90. [see also:] Schlosser, M.; Franzini, L.; Bauer, C.; Leroux, F. Chem. Eur. J. 2001, 7, 1909. doi:10.1002/1521-3765(20010504)7:9<1909::AID- CHEM1909>3.0.CO;2-H
91. Mulzer, J.; Brüntrup, G.; Finke, J.; Zippel, M. J. Am. Chem. Soc. 1979, 101, 7723 doi:10.1021/ja00520a020.
92. Mulzer, J.; Zippel, M.; Brüntrup, G.; Segner, J.; Finke, J. Liebigs Ann. Chem. 1980, 1108. doi:10.1002/jlac.198019800710.
93. Young, D.; Kitching, W. Aust. J. Chem. 1985, 38, 1767
94. Denmark, S.; Weber, E. J.; Wilson, T. M.; Willson, T. M. Tetrahedron 1989, 45, 1053
95. [Review:] Gung, B. W. Org. React. 2004, 64, 1.
96. White, J. M.; Tunoori, A. R.; Georg, G. I. J. Am. Chem. Soc. 2000, 122, 11995 doi:10.1021/ja002149g.
97. Zhao, Y.;Snieckus, V. Unpublished results.
98. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923. doi:10.1021/jo00408a041.
99. Perrin, D. D.; Amarego, W. L.; Mitra, A. Purification of laboratory chemicals, 2nd ed; Pergamon: Oxford, 1980.
100. Winkle, M. R.; Lansinger, J. M.; Ronald, R. C. J. Chem. Soc., Chem. Commun. 1980, 87. doi:10.1039/c39800000087.