Lewis Acid-Induced Chemo- And Stereoselective Allylation of α-Iodo Mixed Acetal with Allylsilane

Journal of Organic Chemistry

Volumn 62, Issue 18, 1997, Pages 6429-6431

  Maeda, Katsuya ^a   Shinokubo, Hiroshi ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000778448     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970753c     Document Type: Article

References (33)

1. Colvin, E. W. Silicon in Organic Synthesis, Butterworth and Co. Ltd.: London, 1981; Chapter 9, pp 97-124.
2. Fleming, I. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, Chapter 2.2, p 563;
3. Yamaguchi, M. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 1, Chapter 1.11, p 325.
4. (a) α-Sulfenyl acetal: Kudo, K.; Hashimoto, Y.; Sukegawa, M.; Hasegawa, M.; Saigo, K. J. Org. Chem. 1993, 58, 579.
5. (b) α-Amino acetal: Polt, R.; Peterson, M. A.; Young, L. D. J. Org. Chem. 1992, 57, 5469.
6. (c) α-Bromo acetal: Mukaiyama, T.; Ishihara, H.; Inomata, K. Chem. Lett. 1975, 527, 531.
7. Recently we have reported the stereoselective synthesis of allyl vinyl ethers from α-iodoacetals: Maeda, K.; Shinokubo, H.; Oshima, K.; Utimoto, K. J. Org. Chem. 1996, 61, 2262.
8. 3) have been reported: Mukaiyama, T.; Ohshima, M.; Miyoshi, N. Chem. Lett. 1987, 1121. Kiyooka, S.; Kaneko, Y.; Komura, M.; Matsuo, H.; Nakano, M. J. Org. Chem. 1991, 56, 2276. Kiyooka, S.; Shirouchi, M.; Kaneko, Y. Tetrahedron Lett. 1993, 34, 1491.
9. 3) have been reported: Mukaiyama, T.; Ohshima, M.; Miyoshi, N. Chem. Lett. 1987, 1121. Kiyooka, S.; Kaneko, Y.; Komura, M.; Matsuo, H.; Nakano, M. J. Org. Chem. 1991, 56, 2276. Kiyooka, S.; Shirouchi, M.; Kaneko, Y. Tetrahedron Lett. 1993, 34, 1491.
10. 3) have been reported: Mukaiyama, T.; Ohshima, M.; Miyoshi, N. Chem. Lett. 1987, 1121. Kiyooka, S.; Kaneko, Y.; Komura, M.; Matsuo, H.; Nakano, M. J. Org. Chem. 1991, 56, 2276. Kiyooka, S.; Shirouchi, M.; Kaneko, Y. Tetrahedron Lett. 1993, 34, 1491.
11. The selective formation of ethers or thioethers from monothioacetals by the appropriate choice of Lewis acid has been reported: Sato, T.; Okura, S.; Otera, J.; Nozaki, H. Tetrahedron Lett. 1987, 28, 6299. Sato, T.; Otera, J.; Nozaki, H. J. Org. Chem. 1990, 55, 6116.
12. The selective formation of ethers or thioethers from monothioacetals by the appropriate choice of Lewis acid has been reported: Sato, T.; Okura, S.; Otera, J.; Nozaki, H. Tetrahedron Lett. 1987, 28, 6299. Sato, T.; Otera, J.; Nozaki, H. J. Org. Chem. 1990, 55, 6116.
13. Stork, G.; Sher, P. M. J. Am. Chem. Soc. 1986, 108, 303.
14. Mukaiyama, T.; Murakami, M. Synthesis 1987, 1043.
15. Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1980, 21, 71; Murata, S.; Suzuki, M.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 3248.
16. Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1980, 21, 71; Murata, S.; Suzuki, M.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 3248.
17. 2 resulted in formation of a small amount of 3a (<15%).
18. For the nomenclature of erythro and threo, see: Noyori, R; Nishida, H. J. Am. Chem. Soc. 1981, 103, 2106.
19. Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1979, 4679.
20. Many mechanistic studies of acetal reactions have been reported: Yamamoto, Y.; Nishii, S.; Yamada, J.-I. J. Am. Chem. Soc. 1986, 108, 7116. Yamamoto, Y.; Yamada, J.-I. J. Chem. Soc. Chem. Commun. 1987, 1218. Murata, S.; Suzuki, M.; Noyori, R. Tetrahedron 1988, 44, 4259. Denmark, S. E.; Wilson, T. M. J. Am. Chem. Soc. 1993, 115, 10695. For a review, see: (a) Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1990, 1, 477.
21. Many mechanistic studies of acetal reactions have been reported: Yamamoto, Y.; Nishii, S.; Yamada, J.-I. J. Am. Chem. Soc. 1986, 108, 7116. Yamamoto, Y.; Yamada, J.-I. J. Chem. Soc. Chem. Commun. 1987, 1218. Murata, S.; Suzuki, M.; Noyori, R. Tetrahedron 1988, 44, 4259. Denmark, S. E.; Wilson, T. M. J. Am. Chem. Soc. 1993, 115, 10695. For a review, see: (a) Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1990, 1, 477.
22. Many mechanistic studies of acetal reactions have been reported: Yamamoto, Y.; Nishii, S.; Yamada, J.-I. J. Am. Chem. Soc. 1986, 108, 7116. Yamamoto, Y.; Yamada, J.-I. J. Chem. Soc. Chem. Commun. 1987, 1218. Murata, S.; Suzuki, M.; Noyori, R. Tetrahedron 1988, 44, 4259. Denmark, S. E.; Wilson, T. M. J. Am. Chem. Soc. 1993, 115, 10695. For a review, see: (a) Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1990, 1, 477.
23. Many mechanistic studies of acetal reactions have been reported: Yamamoto, Y.; Nishii, S.; Yamada, J.-I. J. Am. Chem. Soc. 1986, 108, 7116. Yamamoto, Y.; Yamada, J.-I. J. Chem. Soc. Chem. Commun. 1987, 1218. Murata, S.; Suzuki, M.; Noyori, R. Tetrahedron 1988, 44, 4259. Denmark, S. E.; Wilson, T. M. J. Am. Chem. Soc. 1993, 115, 10695. For a review, see: (a) Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1990, 1, 477.
24. Many mechanistic studies of acetal reactions have been reported: Yamamoto, Y.; Nishii, S.; Yamada, J.-I. J. Am. Chem. Soc. 1986, 108, 7116. Yamamoto, Y.; Yamada, J.-I. J. Chem. Soc. Chem. Commun. 1987, 1218. Murata, S.; Suzuki, M.; Noyori, R. Tetrahedron 1988, 44, 4259. Denmark, S. E.; Wilson, T. M. J. Am. Chem. Soc. 1993, 115, 10695. For a review, see: (a) Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1990, 1, 477.
25. (b) Mash, A. E. In Studies in Natural Product Synthesis; Atta-Ur Rahman, Ed.; Elsevier: Amsterdam, 1988; Vol. 1, p 577.
26. (c) Seebach, D.; Imwinkelried, R.; Weber, T. In Modern Synthetic Methods; Sheffold, R., Ed.; Springer-Verlag; Berlin, 1986; Vol. 4, p 125.
27. 2) in 89% yield.
28. Silanol is more acidic than the corresponding alcohol. Bassindale, A. R.; Taylor, P. G. In The Chemistry of Organic Silicon Compounds Part 1; Patai, S.; Rappoport, Z., Eds.; John Wiley & Sons: Chichester, 1989; Chapter 12, pp 809-838.
29. Silanol is more acidic than the corresponding alcohol. Bassindale, A. R.; Taylor, P. G. In The Chemistry of Organic Silicon Compounds Part 1; Patai, S.; Rappoport, Z., Eds.; John Wiley & Sons: Chichester, 1989; Chapter 12, pp 809-838.
30. Cherest, M.;Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199. Anh, N. T. Topics Curr. Chem. 1980, 88, 145.
31. Cherest, M.;Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199. Anh, N. T. Topics Curr. Chem. 1980, 88, 145.
32. anti-Selective reaction of α-sulfenyl acetals with allylsilane has been reported. See ref 2a.
33. Maeda, K.; Shinokubo, H.; Oshima, K. J. Org. Chem. 1996, 61, 6770.