Stereochemical Studies on the Addition of Allylsilanes to Aldehydes. The SE’ Component
DOI:
https://doi.org/10.29356/jmcs.v53i3.1001Keywords:
Allyllsilanes, Addition to Aldehides, Condensation Reaction, Cyclization, StereochemistryAbstract
Model compounds ul-1 and lk-1 have been studied to determine both the position of the silicon electrofuge and the relative orientation of the double bonds in the transition structure of the allylmetal-aldehyde condensation. The use of the deuterium label allows an unbiased assessment of the syn versus anti SE’ pathways. The synthesis of configurational proof of model systems ul-1 and lk-1 are discussed as well as the cyclization of the model system. Cyclization of model 1 was found to proceed with high selectivity via an anti SE’ pathway regardless of the proximal/distal ratio for all Lewis acids studied. Reactions promoted by fluoride ion favored the proximal product, but both syn and anti pathways were observed.
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References
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2. To effectively describe the products observed in these reactions the stereochemical descriptors suggested by Masamune will be employed: Masamune, S.; Kaiko, T.; Garvey, D. S. J. Am. Chem. Soc. 1982, 104, 5521-5523.
3. Reviews: (a) Hoffmann, R. W. In Stereocontrolled Organic Synthesis; Trost, B. M., Ed.; Blackwell Scientific Publications: Cambridge; 1994; pp 259-274. (b) Roush, W. R. In Stereoselective Synthesis, Methods of Organic Chemistry (Houben-Weyl); E21; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme Stuttgart: New York, 1996; Vol. 3; pp 1410-1486. (c) Hall, D. G.; Lachance, H. Org. React. 2008, 73, 1-573.
4. Reviews: (a) Gung, B. W. Org. React. 2004, 64, 1-413. (b) Yamamoto, Y. Acc. Chem. Res. 1987, 20, 243-249.
5. Reviews: (a) Sakurai, H. Pure Appl. Chem. 1982, 54, 1-22. (b) Majetich, G. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed.; JAI Press: Greenwich, 1989; Vol. 1, p. 173240. (c) Hosomi, A. Acc. Chem. Res. 1988, 21, 200-206. (d) Fleming, I.; Dunogués, J.; Smithers, R. Org. React. 1989, 37, 57575. (e) Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063-2192. (f) Langkopf, E.; Schinzer, D. Chem. Rev. 1995, 95, 1375-1408. (g) Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293-1316. (h) The intramolecular reactions of allylsilanes have also been reviewed: Schinzer, D. Synthesis 1988, 263-273.
6. Reviews: Furstner, A. Chem. Rev. 1999, 99, (4), 991-1045. (b) Cintas, P. Synthesis 1992, 248-257. (c) Avalos, M.; Babiano, R.; Cintas, P.; Jimenez, J. L.; Palacios, J. C., Chem. Soc. Rev. 1999, 28, 169-177. (d) Hargaden, G. C.; Guiry, P. J. Adv. Synth. Catal. 2007, 349, 2407-2424.
7. Reviews: (a) Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807-832. (b) Duthaler, R. O.; Hafner, A.; Alsters, P. L.; RotheStreit, P.; Rihs, G. Pure Appl. Chem. 1992, 64, 1897-1910. (c) Hoppe, D. In Stereoselective Synthesis; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme, Stuttgart: New York, 1995; Vol. E 21b, pp 1551-1583.
8. Denmark, S. E.; Weber, E. J. Helv. Chim. Acta 1983, 66, 16551660.
9. For an early, general discussion of the topological features of reactions of double bonds see: Seebach, D.; Golinski, J. Helv. Chim. Acta 1981, 64, 1413-1423.
10. (a) Li, Y.; Houk, K. N. J. Am. Chem. Soc. 1989, 111, 1236-1240. (b) Gung, B. W.; Xue, X. Tetrahedron: Asymmetry 2001, 12, 2955-2959.
11. (a) Imachi, M.; Nakagawa, J.; Hayashi, M. J. Mol. Struct. 1983, 102, 403-412. (b) Hayashi, M.; Imachi, M.; Saito, M. Chem. Lett. 1977, 221-222. (c) Beagley, B.; Foord, A.; Moutran, R.; Roszondai, B. J. Mol. Struc. 1977, 117-120. (d) Ohno, K.; Toga, K.; Murata, M. Bull. Chem. Soc. Jpn. 1977, 50, 2870-2876.
12. White, J. M.; Clark, C. I. In Topics in Stereochemistry; Denmark, S. E., Ed.; Wiley: New York, 1999; pp 137-200.
13. Kahn, S. D.; Pau, C. F.; Chamberlin, A. R.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 650-663.
14. For a thorough disquisition on the state of the art in SE’ reactions see: Matassa, V. G.; Jenkins, P. R.; Kümin, A.; Damm, L.; Schreiber, J.; Felix, D.; Zass, E.; Eschenmoser, A. Isr. J. Chem. 1989, 29, 321-343.
15. (a) Fleming, I.; Terrett, N. K. Pure Appl. Chem. 1983, 55, 17071713. (b) Fleming, I. Pure Appl. Chem., 1988, 60, 71-78.
16. (a) Carter, M. J.; Fleming, I. J. Chem. Soc. Chem. Commun, 1976, 679-680. (b) Au-Yeung, B.-W.; Fleming, I. J. Chem. Soc. Chem. Commun. 1977, 79-80. (c) Au-Yeung, B.-W.; Fleming, I. J. Chem. Soc. Chem. Commun. 1977, 81. (d) Fleming, I.; Williams, R. V. J. Chem. Soc. Perkin I, 1981, 684-688. (e) Carter, M. J.; Fleming, I.; Percival, A. J. Chem. Soc. Perkin I, 1981, 2415-2434. (f) Chan, T. H.; Fleming, I. Synthesis, 1979, 761-786. (g) Fleming, I.; Au-Yeung, B. -W. Tetrahedron Suppl. 1 1981, 37, 13-24. (h) Fleming, I.; Terrett, N. K. Tetrahedron Lett. 1984, 25, 5103-5104.
17. (a) Fleming, I.; Terrett, N. K. J. Organomet. Chem. 1984, 264, 99-118. (b) Fleming, I. Terrett, N. K. Tetrahedron Lett. 1983, 24, 4153-4156. (c) Chow, H.-F.; Fleming, I. Tetrahedron Lett. 1985, 26, 397-400. (d) Fleming, I.; Sarkar, A. K.; Thomas, A. P. J. Chem. Soc. Chem. Commun. 1987, 157-159.
18. (a) Wetter, H.; Scherer, P.; Schweizer, W. B. Helv. Chim. Acta 1979, 62, 1985-1989. (b) Wetter, H.; Scherer, P. Helv. Chim. Acta 1983, 66, 118-122.
19. (a) Young, D.; Kitching, W. Tetrahedron Lett. 1983, 24, 57935796. (b) Wickham, G.; Kitching, W.J. Org. Chem. 1983, 48, 612-614. (c) Wickham, G.; Kitching, W. Organometallics 1983, 2, 541-547. (d) Young, D.; Kitching, W.; Wickham, G. Tetrahedron Lett. 1983, 24, 5789-5792. (e) Young, D.; Kitching, W. Aust. J. Chem. 1985, 38, 1767-1777. (f) Young, D.; Jones, M.; Kitching, W. Aust. J. Chem. 1986, 39, 563-573. (g) Wickham, G.; Young, D.; Kitching, W. Organometallics 1988, 7, 1187-1195.
20. (a) Hayashi, T.; Konishi, M.; Kumada, M. J. Am. Chem. Soc. 1982, 104, 4963-4965. (b) Hayashi, T.; Konishi, M.; Kumada, M. J. Org. Chem. 1983, 48, 281-282. (c) Hayashi, T.; Ito, H.; Kumada, N. Tetrahedron Lett. 1982, 23, 4605-4606. (d) Hayashi, T.; Okamoto, Y.; Kabeta, K.; Hagihara, T.; Kumada, M. J. Org. Chem. 1984, 49, 4224-4226.
21. Panek, J. S.; Yang, M. J. Am. Chem. Soc. 1991, 113, 9868-9870.
22. (a) Denmark, S. E.; Weber, E. J. J. Am. Chem. Soc. 1984, 106, 7970-7971. (b) Denmark, S. E.; Henke, B. R.; Weber, E. J. J. Am. Chem. Soc. 1987, 109, 2512-2514. (c) Denmark, S. E.; Weber, E. J.; Wilson, T. M.; Willson, T. M. Tetrahedron 1989, 45, 10531065.
23. (a) Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Angew. Chem. Int. Ed. 1990, 29, 256-272. (b) Ooi, T.; Maruoka, K. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; Chapter 1. (c) Saito, S.; Yamamoto, H. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; Chapter 2. (c) Reetz, M. T.; Hüllmann, M.; Massa, W.; Berger, S.; Rademacher, P.; Heymanns, P. J. Am. Chem. Soc. 1986, 108, 2405-2408. (d) Denmark, S. E.; Henke, B. R.; Weber, E. J. Am. Chem. Soc. 1987, 109, 2512-2514. (e) Denmark, S. E.; Almstead, N. G. J. Am. Chem. Soc. 1993, 115, 3133-3139. 24. (a) Keck, G. E.; Castellino, S. J. Am. Chem. Soc. 1986, 108, 3847-3849. (b) Keck, G. E.; Castellino, S.; Wiley, M. R. J. Org. Chem. 1986, 51, 5478-5480. (c) Filippini, F.; Susz, B. -P. Helv. Chim. Acta 1971, 54, 835-845. (d) Beattie, I. R. Quart. Rev. 1963, 17, 382-405.
25. Biddle, M. M.; Reich, H. J. J. Org. Chem. 2006, 71, 4031-4039.
26. (a) Fleming, I.; Terrett, N. K. J. Organomet. Chem. 1984, 264, 99-118. (b) Fleming, I. Terrett, N. K. Tetrahedron Lett. 1983, 24, 4153-4156. (c) Chow, H.-F.; Fleming, I. Tetrahedron Lett. 1985, 26, 397-400. (d) Fleming, I.; Sarkar, A. K.; Thomas, A. P. J. Chem. Soc. Chem. Commun. 1987, 157-159.
27. Gerlach, H.; Mueller, W. Angew. Chem. Int. Ed. Engl. 1972, 11, 1030-1031.
28. (a) Smithers, R. H. J. Org. Chem. 1978, 43, 2833-2838. (b) Matsumoto, M.; Kuroda, K. Tetrahedron Lett. 1980, 21, 40214024.
29. (a) Bachman, G. B. J. Am. Chem. Soc. 1933, 55, 4279-4284. (b) Farrell, J. K.; Bachman, G. B. J. Am. Chem. Soc. 1935, 57, 12811283.
30. (a) Wolinsky, J.; Erickson, K. L. J. Org. Chem. 1965, 30, 22082211. (b) Dawson, T. M.; Dixon, J.; Littlewood, R. S.; Lythgoe, B. J. Org. Chem. 1971, 2352-2355.
31. Wadsworth, W. S. Org. React. 1977, 25, 73-253.
32. (a) Tomboulian, P.; Stehower, K. J. Org. Chem. 1968, 33, 15091512. (b) House, H. O.; Trost, B. M. J. Org. Chem. 1965, 30, 1341-1348.
33. Reider, P. J.; Eichen Conn, R.; S.; Davis, P.; Grenda, V. J.; Zambito, A. J.; Grabowski, E. J. J. J. Org. Chem. 1987, 52, 33263334.
34. The stereochemical families are defined by the Seebach-Prelog recommendations by consideration of the two stereocenters of the allylsilane: Seebach, D.; Prelog, V. Angew. Chem. Int. Ed. Engl. 1982, 21, 654-660.
35. Ratcliffe, R.; Rodehorst, R. J. Org. Chem. 1970, 35, 4000-4002.
36. The configuration of the hydroxyl group was assigned on the basis of the slope of the LIS of the methylidene group with Eu(fod)3: syn-2, 6.61 ppm/equiv.; anti-2, 2.81 ppm/equiv. See reference 8. 37. (a) Middleton, W. J. Org. Syn. 1985, 64, 221-225. (b) Szarek, W. A.; Hay, G. W.; Dozoszewski, B. J. Chem. Soc., Chem. Commun. 1985, 663-664.
38. (a) Hosomi, A.; Shirahata, A.; Sakurai, H. Tetrahedron Lett. 1978, 3043-3046. (b) Hosomi, A.; Shirahata, A.; Sakurai, H. Chem. Lett. 1978, 901-904.
39. DePuy, C. H.; Bierbaum, V. M.; Flippin, L. A.; Grabowski, J. J.; King, G. K.; Schmitt, R. J.; Sullivan, S. A. J. Am. Chem. Soc. 1980, 102, 5012-5015.
40. (a) Majetich, G.; Casares, A.; Chapman, D.; Behnke, M. J. Org. Chem. 1986, 51, 1745-1753. (b) Majetich, G.; Desmond, R. W. Jr.; Soria, J. J. J. Org. Chem. 1986, 51, 1753-1769.
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42. This conclusion assumes that the rotation of the terminal methylene group of the allyl anion is faster than addition to the aldehyde.
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