'Halophilic activation' of chlorosilanes: Allylation of aldehydes catalyzed by platinum dichloride or silver triflate

Synthesis

Volumn , Issue 7, 2000, Pages 959-969

  Fürstner, Alois ^a   Voigtländer, David ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

Addition reactions; Alcohols; Aldehydes; Allylation; Catalysis; Platinum; Silicon; Silver

Indexed keywords

PLATINUM DERIVATIVE; SILANE DERIVATIVE; SILVER DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; GERMANY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0042347222     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2000-6290     Document Type: Article

References (58)

1. For general and comprehensive reviews see: (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
2. (b) Fleming, I.; Dunogues, J.; Smithers, R. Org. React. 1989, 37, 57.
3. (c) Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293.
4. Hosomi, A.; Sakurai, H. Tetrahedron Lett. 1976, 1295.
5. There are, however, some exceptions to this rule. For leading references on Sakurai-type reactions using catalytic amounts of Lewis or Bronsted acids see among others: (a) Davis, A. P.; Jaspars, M. Chem. Commun. 1990, 1176.
6. (b) Komatsu, N.; Uda, M.; Suzuki, H.; Takahashi, T.; Domae, T.; Wada, M. Tetrahedron Lett. 1997, 38, 7215.
7. (c) Aggarwal, V. K.; Vennall, G. P. Synthesis 1998, 1822.
8. (d) Mukaiyama, T.; Nagaoka, H.; Murakami, M.; Ohshima, M. Chem. Lett. 1985, 977.
9. (e) Hollis, T. K.; Bosnich, B. J. Am. Chem. Soc. 1995, 117, 4570.
10. (f) Marx, A.; Yamamoto, H. Angew. Chem. Int. Ed. 2000, 39, 178.
11. For enantioselective Sakurai reactions using stoichiometric or catalytic amounts of chiral Lewis acids see the following for leading references: (a) Gauthier, D. R.; Carreira, E. M. Angew. Chem. Int. Ed. Engl. 1996, 35, 2363.
12. (b) Ishihara, K.; Mouri, M.; Gao, Q.; Maruyama, T.; Furuta, K.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 11490.
13. (c) Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S.-I. J. Am. Chem. Soc. 1998, 120, 6419.
14. (d) Yanagisawa, A.; Kageyama, H.; Nakatsuka, Y.; Asakawa, K.; Matsumoto, Y.; Yamamoto, H. Angew. Chem. Int. Ed. 1999, 38, 3707.
15. This mechanistic rationale was originally proposed by: Hayashi, T.; Kabeta, K.; Hamachi, I.; Kumada, M. Tetrahedron Lett. 1983, 24, 2865.
16. For pertinent reviews, see: (a) Sakurai, H. Synlett 1989, 1.
17. (b) Marshall, J. A. Chemtracts - Organic Chemistry 1998, 11, 697.
18. Kobayashi, S.; Nishio, K. J. Org. Chem. 1994, 59, 6620.
19. See the following for leading references: (a) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron 1999, 55, 977.
20. (b) Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S.-I. J. Am. Chem. Soc. 1998, 120, 6419.
21. (c) Wang, D.; Wang, Z. G.; Wang, M. W.; Chen, Y. J.; Liu, L., Zhu, Y. Tetrahedron: Asymm. 1999, 10, 327.
22. (d) Chataigner, I.; Piarulli, U.; Gennari, C. Tetrahedron Lett. 1999, 40, 3633.
23. (a) Hosomi, A.; Shirahata, A.; Sakurai, H. Tetrahedron Lett. 1978, 3043.
24. (b) For recent advancements see i. a.: Asao, N.; Shibato, A.; Itagaki, Y.; Jourdan, F.; Maruoka, K. Tetrahedron Lett. 1998, 39, 3177.
25. Nakamura, K.; Nakamura, H.; Yamamoto, Y. J. Org. Chem. 1999, 64, 2614.
26. Hagen, G.; Mayr, H. J. Am. Chem. Soc. 1991, 113, 4954.
27. "Free" silylium cations cannot be expected in condensed phase; for a review on the silylium ion problem see: Reed, C. A. Acc. Chem. Res. 1998, 31, 325.
28. 2: Iwasawa, N.; Mukaiyama, T. Chem. Lett. 1987, 463.
29. 3: Mukaiyama, T.; Ohno, T.; Nishimura, T.; Han, J. S.; Kobayashi, S. Chem. Lett. 1990, 2239.
30. A similar array formed by a different approach is discussed as reactive intermediate in: Frost, L. M.; Smith, J. D.; Berrisford, D. J. Tetrahedron Lett. 1999, 40, 2183.
31. Short review on the use of AgOTf in synthesis: Black, T. H. In Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A., Ed., Wiley, New York, 1995, p 4476.
32. In line with Scheme 4, pure allyldimethylsilyl triflate (2) was also found to catalyze the addition of 1 to aldehydes with similar ease and efficiency. Due to its very hygroscopic character, this compound is difficult to handle and its in situ preparation from 1 and AgOTf is therefore highly advantageous from the preparative point of view.
33. Allyldimethylsilyl triflate (2) has been previously used in stoichiometric amounts for the allylation of p-methoxybenzaldehyde which is assumed to proceed via the same cationic 6-membered transition state as shown in Scheme 4, cf.: Brook, M. A.; Crowe, G. D.; Hiemstra, H. Can. J. Chem. 1994, 72, 264.
34. 2O (41%), DMF (27%), DMSO (no reaction).
35. (a) Salimgareeva, I. M.; Zhebarov, O. Z.; Bogatova, N. G.; Lakhtin, V. G.; Yurev, V. P. Iz. Akad. Nauk. SSSR Ser. Kim. 1980, 2, 407; Chem. Abstr. 1980, 92, 181268.
36. (a) Salimgareeva, I. M.; Zhebarov, O. Z.; Bogatova, N. G.; Lakhtin, V. G.; Yurev, V. P. Iz. Akad. Nauk. SSSR Ser. Kim. 1980, 2, 407; Chem. Abstr. 1980, 92, 181268.
37. (b) Uyeo, S.; Itani, H. Tetrahedron Lett. 1991, 32, 2143.
38. Bismara, C.; Di Fabio, R.; Donati, D.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1995, 36, 4283.
39. Ojima, I.; Kumagai, M. J. Organomet. Chem. 1987, 157, 359.
40. Petrov, A. D.; Nikishin, G. I. Iz. Akad. Nauk. SSSR Ser. Kim. 1956, 243; English Translation: 1956, 233; Chem. Abstr. 1956, 50, 13726.
41. Petrov, A. D.; Nikishin, G. I. Iz. Akad. Nauk. SSSR Ser. Kim. 1956, 243; English Translation: 1956, 233; Chem. Abstr. 1956, 50, 13726.
42. 2 merely acts as a "conventional" Lewis acid and triggers the allylation by coordination onto the aldehyde via a regular Hosomi-Sakurai type process.
43. 2 as catalyst in cycloisomerization reactions see: Fürstner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305.
44. Kira, M.; Hino, T.; Sakurai, H. Tetrahedron Lett. 1989, 30, 1099.
45. Chang, Y.-H.; Uang, B.-J.; Wu, C.-M.; Yu, T.-H. Synthesis 1990, 1033.
46. Takahara, J. P.; Masuyama, Y.; Kurusu, Y. J. Am. Chem. Soc. 1992, 114, 2577.
47. Jones, P; Knochel, P. J. Org. Chem. 1999, 64, 186.
48. Davis, A. P.; Jaspars, M. J. Chem. Soc., Perkin Trans. 1 1992, 2111.
49. Chalecki, Z.; Guibé-Jampel, E.; Plenkiewicz, J. Synth. Commun. 1997, 27, 1217.
50. Hosomi, A.; Kohra, S.; Ogata, K.; Yanagi, T.; Tominaga, Y. J. Org. Chem. 1990, 55, 2415.
51. Asao, N.; Liu, P.; Maruoka, K. Angew. Chem. Int. Ed. Engl. 1997, 36, 2507.
52. Heathcock, C. H.; Kiyooka, S.-I.; Blumenkopf, T. A. J. Org. Chem. 1984, 49, 4214.
53. Hermans, B.; Hevesi, L. J. Org. Chem. 1995, 60, 6141.
54. Hunter, R.; Michael, J. P.; Tomlinson, G. D. Tetrahedron 1994, 50, 871.
55. Fürstner, A.; Brunner, H. Tetrahedron Lett. 1996, 37, 7009.
56. Takai, K.; Toratsu, C. J. Org. Chem. 1998, 63, 6450.
57. Fürstner, A.; Shi, N. J. Am. Chem. Soc. 1996, 118, 12349.
58. Ren, P.-D.; Shao, D.; Dong, T.-W. Synth. Commun. 1997, 27, 2569.