Stereoselective synthesis of allyl vinyl ethers from silyl enol ethers

Journal of Organic Chemistry

Volumn 61, Issue 7, 1996, Pages 2262-2263

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

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001631795     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960289w     Document Type: Article

References (33)

1. Recent reviews: (a) Bartlett, P. A. Tetrahedron 1980, 36, 3. (b) Gajewski, J. J. Hydrocarbon Thermal Isomerizations; Academic Press: New York, 1981. (c) Lutz, R. P. Chem. Rev. 1984, 84, 205. (d) Hill, R. K. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984: Vol. 3, p 503. (e) Murray, A. W. Org. React. Mech. 1986, 429; 1987, 457. (f) Moody, C. J. Adv. Heterocycl. Chem. 1987, 42, 203. (g) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (h) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (i) Blechert, S. Synthesis 1989, 71. (j) Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: New York, 1991; Vol. 5, Chapter 7.2, p 827.
2. Recent reviews: (a) Bartlett, P. A. Tetrahedron 1980, 36, 3. (b) Gajewski, J. J. Hydrocarbon Thermal Isomerizations; Academic Press: New York, 1981. (c) Lutz, R. P. Chem. Rev. 1984, 84, 205. (d) Hill, R. K. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984: Vol. 3, p 503. (e) Murray, A. W. Org. React. Mech. 1986, 429; 1987, 457. (f) Moody, C. J. Adv. Heterocycl. Chem. 1987, 42, 203. (g) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (h) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (i) Blechert, S. Synthesis 1989, 71. (j) Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: New York, 1991; Vol. 5, Chapter 7.2, p 827.
3. Recent reviews: (a) Bartlett, P. A. Tetrahedron 1980, 36, 3. (b) Gajewski, J. J. Hydrocarbon Thermal Isomerizations; Academic Press: New York, 1981. (c) Lutz, R. P. Chem. Rev. 1984, 84, 205. (d) Hill, R. K. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984: Vol. 3, p 503. (e) Murray, A. W. Org. React. Mech. 1986, 429; 1987, 457. (f) Moody, C. J. Adv. Heterocycl. Chem. 1987, 42, 203. (g) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (h) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (i) Blechert, S. Synthesis 1989, 71. (j) Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: New York, 1991; Vol. 5, Chapter 7.2, p 827.
4. Recent reviews: (a) Bartlett, P. A. Tetrahedron 1980, 36, 3. (b) Gajewski, J. J. Hydrocarbon Thermal Isomerizations; Academic Press: New York, 1981. (c) Lutz, R. P. Chem. Rev. 1984, 84, 205. (d) Hill, R. K. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984: Vol. 3, p 503. (e) Murray, A. W. Org. React. Mech. 1986, 429; 1987, 457. (f) Moody, C. J. Adv. Heterocycl. Chem. 1987, 42, 203. (g) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (h) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (i) Blechert, S. Synthesis 1989, 71. (j) Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: New York, 1991; Vol. 5, Chapter 7.2, p 827.
5. Recent reviews: (a) Bartlett, P. A. Tetrahedron 1980, 36, 3. (b) Gajewski, J. J. Hydrocarbon Thermal Isomerizations; Academic Press: New York, 1981. (c) Lutz, R. P. Chem. Rev. 1984, 84, 205. (d) Hill, R. K. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984: Vol. 3, p 503. (e) Murray, A. W. Org. React. Mech. 1986, 429; 1987, 457. (f) Moody, C. J. Adv. Heterocycl. Chem. 1987, 42, 203. (g) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (h) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (i) Blechert, S. Synthesis 1989, 71. (j) Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: New York, 1991; Vol. 5, Chapter 7.2, p 827.
6. Recent reviews: (a) Bartlett, P. A. Tetrahedron 1980, 36, 3. (b) Gajewski, J. J. Hydrocarbon Thermal Isomerizations; Academic Press: New York, 1981. (c) Lutz, R. P. Chem. Rev. 1984, 84, 205. (d) Hill, R. K. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984: Vol. 3, p 503. (e) Murray, A. W. Org. React. Mech. 1986, 429; 1987, 457. (f) Moody, C. J. Adv. Heterocycl. Chem. 1987, 42, 203. (g) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (h) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (i) Blechert, S. Synthesis 1989, 71. (j) Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: New York, 1991; Vol. 5, Chapter 7.2, p 827.
7. Recent reviews: (a) Bartlett, P. A. Tetrahedron 1980, 36, 3. (b) Gajewski, J. J. Hydrocarbon Thermal Isomerizations; Academic Press: New York, 1981. (c) Lutz, R. P. Chem. Rev. 1984, 84, 205. (d) Hill, R. K. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984: Vol. 3, p 503. (e) Murray, A. W. Org. React. Mech. 1986, 429; 1987, 457. (f) Moody, C. J. Adv. Heterocycl. Chem. 1987, 42, 203. (g) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (h) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (i) Blechert, S. Synthesis 1989, 71. (j) Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: New York, 1991; Vol. 5, Chapter 7.2, p 827.
8. Recent reviews: (a) Bartlett, P. A. Tetrahedron 1980, 36, 3. (b) Gajewski, J. J. Hydrocarbon Thermal Isomerizations; Academic Press: New York, 1981. (c) Lutz, R. P. Chem. Rev. 1984, 84, 205. (d) Hill, R. K. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984: Vol. 3, p 503. (e) Murray, A. W. Org. React. Mech. 1986, 429; 1987, 457. (f) Moody, C. J. Adv. Heterocycl. Chem. 1987, 42, 203. (g) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (h) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (i) Blechert, S. Synthesis 1989, 71. (j) Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: New York, 1991; Vol. 5, Chapter 7.2, p 827.
9. Recent reviews: (a) Bartlett, P. A. Tetrahedron 1980, 36, 3. (b) Gajewski, J. J. Hydrocarbon Thermal Isomerizations; Academic Press: New York, 1981. (c) Lutz, R. P. Chem. Rev. 1984, 84, 205. (d) Hill, R. K. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984: Vol. 3, p 503. (e) Murray, A. W. Org. React. Mech. 1986, 429; 1987, 457. (f) Moody, C. J. Adv. Heterocycl. Chem. 1987, 42, 203. (g) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (h) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (i) Blechert, S. Synthesis 1989, 71. (j) Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: New York, 1991; Vol. 5, Chapter 7.2, p 827.
10. Recent reviews: (a) Bartlett, P. A. Tetrahedron 1980, 36, 3. (b) Gajewski, J. J. Hydrocarbon Thermal Isomerizations; Academic Press: New York, 1981. (c) Lutz, R. P. Chem. Rev. 1984, 84, 205. (d) Hill, R. K. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984: Vol. 3, p 503. (e) Murray, A. W. Org. React. Mech. 1986, 429; 1987, 457. (f) Moody, C. J. Adv. Heterocycl. Chem. 1987, 42, 203. (g) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (h) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (i) Blechert, S. Synthesis 1989, 71. (j) Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: New York, 1991; Vol. 5, Chapter 7.2, p 827.
11. Recent reviews: (a) Bartlett, P. A. Tetrahedron 1980, 36, 3. (b) Gajewski, J. J. Hydrocarbon Thermal Isomerizations; Academic Press: New York, 1981. (c) Lutz, R. P. Chem. Rev. 1984, 84, 205. (d) Hill, R. K. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984: Vol. 3, p 503. (e) Murray, A. W. Org. React. Mech. 1986, 429; 1987, 457. (f) Moody, C. J. Adv. Heterocycl. Chem. 1987, 42, 203. (g) Ziegler, F. E. Chem. Rev. 1988, 88, 1423. (h) Kallmerten, J.; Wittman, M. D. Stud. Nat. Prod. Chem. 1989, 3, 233. (i) Blechert, S. Synthesis 1989, 71. (j) Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: New York, 1991; Vol. 5, Chapter 7.2, p 827.
12. Sugihara, M.; Yanagisawa, M.; Nakai, T. Synlett 1995, 447, Ziegler, F. E. Acc. Chem. Res. 1977, 10, 227.
13. Sugihara, M.; Yanagisawa, M.; Nakai, T. Synlett 1995, 447, Ziegler, F. E. Acc. Chem. Res. 1977, 10, 227.
14. The Tebbe reagent has been used to prepare allyl vinyl ether. Kinney, W. A., Coghlan, M. J.; Paquette, L. A. J. Am. Chem. Soc. 1985, 107, 7352.
15. 4 system has been reported previously. Okazoe, T.; Takai, K.; Oshima, K.; Utimoto, K. J. Org. Chem. 1987, 52, 4410.
16. Thiem, J.; Karl, H.; Schwenmer, J. Synthesis 1978, 696.
17. For a related procedure, see: Stork, G.; Sher, P. M. J. Am. Chem. Soc. 1986, 108, 303.
18. The use of (trimethylsiloxy)ethene in place of (tert-butyldimethylsiloxy)lethene gave an α-iodocarbonyl compound upon treatment with NIS in the presence of alcohols. Reaction of trimethylsilyl enol ethers with NCS has been reported to give α-chloro ketones. Hambly, G. F.; Chan, T. H. Tetrahedron Lett. 1986, 27, 2563.
19. 2SiCl and DBU. Taniguchi, Y.; Inanaga, J.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1981, 54, 3229
20. 2SiCl and DBU. Taniguchi, Y.; Inanaga, J.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1981, 54, 3229
21. 2SiCl and DBU. Taniguchi, Y.; Inanaga, J.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1981, 54, 3229
22. 2SiCl and DBU. Taniguchi, Y.; Inanaga, J.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1981, 54, 3229
23. For the nomenclature of threo and erythro, see: Noyori, R.; Nishida, H. J. Am. Chem. Soc. 1981, 103, 2106.
24. 4 and concentrated in vacuo. The residual oil was applied to an alumina (ICN alumina B activity III) column to give 3aA (0.11 g) at a yield of 66% along with (tert-butyldimethylsiloxy)ethene (8%).
25. The conversion of halo ether or halo acetal to alkene or alkenyl ether with n-BuLi or t-BuLi has been reported in the total synthesis of natural products. Wender, P. A.; Keenan, R. M.; Lee, H. Y. J. Am. Chem. Soc. 1987, 109, 4390. Ireland, R. E.; Habich, D.; Norbech, D. W. J. Am. Chem. Soc. 1985, 107, 3271.
26. The conversion of halo ether or halo acetal to alkene or alkenyl ether with n-BuLi or t-BuLi has been reported in the total synthesis of natural products. Wender, P. A.; Keenan, R. M.; Lee, H. Y. J. Am. Chem. Soc. 1987, 109, 4390. Ireland, R. E.; Habich, D.; Norbech, D. W. J. Am. Chem. Soc. 1985, 107, 3271.
27. It is not clear why the siloxy group was eliminated prior to the allyloxy group. Selective elimination of the siloxy group may have occurred because silanol has a higher acidity than alcohols. Bassindale, A. R.; Taylor, P. G. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons, Ltd.: New York, 1989; Part 1, Chapter 12, pp 809-838.
28. 15 (Equation Presented)
29. Takai, K.; Mori, I.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1984, 57 446. Nonoshita, K.; Banno, H.; Maruoka, K.; Yamamoto, H. J. Am. Chem, Soc. 1990, 112, 316. Maruoka, K.; Saito, S.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 1165.
30. Takai, K.; Mori, I.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1984, 57 446. Nonoshita, K.; Banno, H.; Maruoka, K.; Yamamoto, H. J. Am. Chem, Soc. 1990, 112, 316. Maruoka, K.; Saito, S.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 1165.
31. Takai, K.; Mori, I.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1984, 57 446. Nonoshita, K.; Banno, H.; Maruoka, K.; Yamamoto, H. J. Am. Chem, Soc. 1990, 112, 316. Maruoka, K.; Saito, S.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 1165.
32. Gilbert, J. C.; Kelley, T. A. Tetrahedron 1388, 44, 7587.
33. The yield of the product could not be determined because of its volatility.