Lithium dienolate generation by α-regioselective reaction of (1-silylallyl)lithiums with carbon monoxide

Organometallics

Volumn 15, Issue 26, 1996, Pages 5459-5461

  Ryu, Ilhyong ^a   Yamamoto, Haruhiko ^a   Sonoda, Noboru ^a   Murai, Shinji ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001564286     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9608014     Document Type: Article

References (26)

1. Murai, S.; Ryu, I.; Iriguchi, J.; Sonoda, N. J. Am. Chem. Soc. 1984, 106, 2440.
2. For other intramolecular conversions of acyl- and aroyllithiums, see: (a) Ryu, I.; Hayama, Y.; Hirai, A.; Sonoda, N.; Orita, A.; Ohe, K.; Murai, S. J. Am. Chem. Soc. 1990, 112, 7061.
3. (b) Orita, A.; Ohe, K.; Murai, S. Organometallics 1994, 13, 1533.
4. (c) Orita, A.; Fukudome, M.; Ohe, K.; Murai, S. J. Org. Chem. 1994, 59, 477.
5. (d) Kai, H.; Iwamoto, K.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 1996, 118, 7634.
6. (e) Smith, K.; Pritchard, G. J. Angew. Chem., Int. Ed. Engl. 1990, 29, 282.
7. Also see intermolecular reactions: (f) Seyferth, D.; Hui, R. C.; Wang, W.-L. J. Org. Chem. 1993, 58, 5843 and references cited therein.
8. For reviews, see: (a) Chan, T. H.; Wang, D. Chem. Rev. 1995, 95, 1279. (b) Panek, J. S. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 1, Chapter 2.5. (c) Yamamoto, Y. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, Chapter 1.2. Also see: (d) Schaunamn, E.; Krischning, A. Tetrahedron Lett. 1988, 29, 4281. (e) Horvath, R. F.; Chan, T. H. J. Org. Chem. 1989, 54, 317. (f) Blanco, F. J.; Cuadrado, F.; Gonzalez, A. M.; Pulido, F. J. Synthesis 1996, 42.
9. For reviews, see: (a) Chan, T. H.; Wang, D. Chem. Rev. 1995, 95, 1279. (b) Panek, J. S. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 1, Chapter 2.5. (c) Yamamoto, Y. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, Chapter 1.2. Also see: (d) Schaunamn, E.; Krischning, A. Tetrahedron Lett. 1988, 29, 4281. (e) Horvath, R. F.; Chan, T. H. J. Org. Chem. 1989, 54, 317. (f) Blanco, F. J.; Cuadrado, F.; Gonzalez, A. M.; Pulido, F. J. Synthesis 1996, 42.
10. For reviews, see: (a) Chan, T. H.; Wang, D. Chem. Rev. 1995, 95, 1279. (b) Panek, J. S. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 1, Chapter 2.5. (c) Yamamoto, Y. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, Chapter 1.2. Also see: (d) Schaunamn, E.; Krischning, A. Tetrahedron Lett. 1988, 29, 4281. (e) Horvath, R. F.; Chan, T. H. J. Org. Chem. 1989, 54, 317. (f) Blanco, F. J.; Cuadrado, F.; Gonzalez, A. M.; Pulido, F. J. Synthesis 1996, 42.
11. For reviews, see: (a) Chan, T. H.; Wang, D. Chem. Rev. 1995, 95, 1279. (b) Panek, J. S. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 1, Chapter 2.5. (c) Yamamoto, Y. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, Chapter 1.2. Also see: (d) Schaunamn, E.; Krischning, A. Tetrahedron Lett. 1988, 29, 4281. (e) Horvath, R. F.; Chan, T. H. J. Org. Chem. 1989, 54, 317. (f) Blanco, F. J.; Cuadrado, F.; Gonzalez, A. M.; Pulido, F. J. Synthesis 1996, 42.
12. For reviews, see: (a) Chan, T. H.; Wang, D. Chem. Rev. 1995, 95, 1279. (b) Panek, J. S. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 1, Chapter 2.5. (c) Yamamoto, Y. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, Chapter 1.2. Also see: (d) Schaunamn, E.; Krischning, A. Tetrahedron Lett. 1988, 29, 4281. (e) Horvath, R. F.; Chan, T. H. J. Org. Chem. 1989, 54, 317. (f) Blanco, F. J.; Cuadrado, F.; Gonzalez, A. M.; Pulido, F. J. Synthesis 1996, 42.
13. For reviews, see: (a) Chan, T. H.; Wang, D. Chem. Rev. 1995, 95, 1279. (b) Panek, J. S. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 1, Chapter 2.5. (c) Yamamoto, Y. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, Chapter 1.2. Also see: (d) Schaunamn, E.; Krischning, A. Tetrahedron Lett. 1988, 29, 4281. (e) Horvath, R. F.; Chan, T. H. J. Org. Chem. 1989, 54, 317. (f) Blanco, F. J.; Cuadrado, F.; Gonzalez, A. M.; Pulido, F. J. Synthesis 1996, 42.
14. The reaction conducted in a THF solution afforded a mixture of more than 10 products which were incorporated by CO.
15. 8) δ 0.02 (s, 9H), 4.50 (dd, J = 12, 2 Hz, 1H), 4.70 (dd, J = 17, 2 Hz, 1H), 5.30 (d, J = 12 Hz, 1H), 5.80-6.10 (m, 1H). For an NMR study of 1-(silyl)allyllithium, see: Fraenkel, G.; Chow, A.; Winchester, W. R. J. Am. Chem. Soc. 1990, 112, 2582.
16. 4, and evaporation of the solvents, the residual oil was purified by bulb to bulb distillation yielding 3b (0.914 g, 75%) as a clear oil.
17. The overall procedure provides a unique [3 + 1] protocol for the synthesis of α,β-unsaturated aldehydes.
18. α,β-Unsaturated acylsilanes are potent synthetic intermediates; for examples, see: (a) Reich, H. J.; Olson, R. E.; Clark, M. C. J. Am. Chem. Soc. 1980, 102, 1423. (b) Reich, H. J.; Eisenhart, E. K. J. Org. Chem. 1984, 49, 5282. (c) Miller, J. A.; Zweifel, G. J. Am. Chem. Soc. 1981, 103, 6217. (d) Sato, T.; Arai, M.; Kuwajima, I. J. Am. Chem. Soc. 1977, 99, 5827. (e) Danheiser, R. L.; Fink, D. M.; Okana, K.; Tsai, Y.-M.; Szczepanski, S. W. J. Org. Chem. 1985, 50, 5393. (f) Nowick, J. S.; Danheiser, R. L. J. Org. Chem. 1989, 54, 2798. (g) For the use of 3a, see: Ogoshi, S.; Ohe, K.; Chatani, N.; Kurosawa, H.; Kawasaki, Y.; Murai, S. Organometallics 1990, 9, 3021.
19. α,β-Unsaturated acylsilanes are potent synthetic intermediates; for examples, see: (a) Reich, H. J.; Olson, R. E.; Clark, M. C. J. Am. Chem. Soc. 1980, 102, 1423. (b) Reich, H. J.; Eisenhart, E. K. J. Org. Chem. 1984, 49, 5282. (c) Miller, J. A.; Zweifel, G. J. Am. Chem. Soc. 1981, 103, 6217. (d) Sato, T.; Arai, M.; Kuwajima, I. J. Am. Chem. Soc. 1977, 99, 5827. (e) Danheiser, R. L.; Fink, D. M.; Okana, K.; Tsai, Y.-M.; Szczepanski, S. W. J. Org. Chem. 1985, 50, 5393. (f) Nowick, J. S.; Danheiser, R. L. J. Org. Chem. 1989, 54, 2798. (g) For the use of 3a, see: Ogoshi, S.; Ohe, K.; Chatani, N.; Kurosawa, H.; Kawasaki, Y.; Murai, S. Organometallics 1990, 9, 3021.
20. α,β-Unsaturated acylsilanes are potent synthetic intermediates; for examples, see: (a) Reich, H. J.; Olson, R. E.; Clark, M. C. J. Am. Chem. Soc. 1980, 102, 1423. (b) Reich, H. J.; Eisenhart, E. K. J. Org. Chem. 1984, 49, 5282. (c) Miller, J. A.; Zweifel, G. J. Am. Chem. Soc. 1981, 103, 6217. (d) Sato, T.; Arai, M.; Kuwajima, I. J. Am. Chem. Soc. 1977, 99, 5827. (e) Danheiser, R. L.; Fink, D. M.; Okana, K.; Tsai, Y.-M.; Szczepanski, S. W. J. Org. Chem. 1985, 50, 5393. (f) Nowick, J. S.; Danheiser, R. L. J. Org. Chem. 1989, 54, 2798. (g) For the use of 3a, see: Ogoshi, S.; Ohe, K.; Chatani, N.; Kurosawa, H.; Kawasaki, Y.; Murai, S. Organometallics 1990, 9, 3021.
21. α,β-Unsaturated acylsilanes are potent synthetic intermediates; for examples, see: (a) Reich, H. J.; Olson, R. E.; Clark, M. C. J. Am. Chem. Soc. 1980, 102, 1423. (b) Reich, H. J.; Eisenhart, E. K. J. Org. Chem. 1984, 49, 5282. (c) Miller, J. A.; Zweifel, G. J. Am. Chem. Soc. 1981, 103, 6217. (d) Sato, T.; Arai, M.; Kuwajima, I. J. Am. Chem. Soc. 1977, 99, 5827. (e) Danheiser, R. L.; Fink, D. M.; Okana, K.; Tsai, Y.-M.; Szczepanski, S. W. J. Org. Chem. 1985, 50, 5393. (f) Nowick, J. S.; Danheiser, R. L. J. Org. Chem. 1989, 54, 2798. (g) For the use of 3a, see: Ogoshi, S.; Ohe, K.; Chatani, N.; Kurosawa, H.; Kawasaki, Y.; Murai, S. Organometallics 1990, 9, 3021.
22. α,β-Unsaturated acylsilanes are potent synthetic intermediates; for examples, see: (a) Reich, H. J.; Olson, R. E.; Clark, M. C. J. Am. Chem. Soc. 1980, 102, 1423. (b) Reich, H. J.; Eisenhart, E. K. J. Org. Chem. 1984, 49, 5282. (c) Miller, J. A.; Zweifel, G. J. Am. Chem. Soc. 1981, 103, 6217. (d) Sato, T.; Arai, M.; Kuwajima, I. J. Am. Chem. Soc. 1977, 99, 5827. (e) Danheiser, R. L.; Fink, D. M.; Okana, K.; Tsai, Y.-M.; Szczepanski, S. W. J. Org. Chem. 1985, 50, 5393. (f) Nowick, J. S.; Danheiser, R. L. J. Org. Chem. 1989, 54, 2798. (g) For the use of 3a, see: Ogoshi, S.; Ohe, K.; Chatani, N.; Kurosawa, H.; Kawasaki, Y.; Murai, S. Organometallics 1990, 9, 3021.
23. α,β-Unsaturated acylsilanes are potent synthetic intermediates; for examples, see: (a) Reich, H. J.; Olson, R. E.; Clark, M. C. J. Am. Chem. Soc. 1980, 102, 1423. (b) Reich, H. J.; Eisenhart, E. K. J. Org. Chem. 1984, 49, 5282. (c) Miller, J. A.; Zweifel, G. J. Am. Chem. Soc. 1981, 103, 6217. (d) Sato, T.; Arai, M.; Kuwajima, I. J. Am. Chem. Soc. 1977, 99, 5827. (e) Danheiser, R. L.; Fink, D. M.; Okana, K.; Tsai, Y.-M.; Szczepanski, S. W. J. Org. Chem. 1985, 50, 5393. (f) Nowick, J. S.; Danheiser, R. L. J. Org. Chem. 1989, 54, 2798. (g) For the use of 3a, see: Ogoshi, S.; Ohe, K.; Chatani, N.; Kurosawa, H.; Kawasaki, Y.; Murai, S. Organometallics 1990, 9, 3021.
24. α,β-Unsaturated acylsilanes are potent synthetic intermediates; for examples, see: (a) Reich, H. J.; Olson, R. E.; Clark, M. C. J. Am. Chem. Soc. 1980, 102, 1423. (b) Reich, H. J.; Eisenhart, E. K. J. Org. Chem. 1984, 49, 5282. (c) Miller, J. A.; Zweifel, G. J. Am. Chem. Soc. 1981, 103, 6217. (d) Sato, T.; Arai, M.; Kuwajima, I. J. Am. Chem. Soc. 1977, 99, 5827. (e) Danheiser, R. L.; Fink, D. M.; Okana, K.; Tsai, Y.-M.; Szczepanski, S. W. J. Org. Chem. 1985, 50, 5393. (f) Nowick, J. S.; Danheiser, R. L. J. Org. Chem. 1989, 54, 2798. (g) For the use of 3a, see: Ogoshi, S.; Ohe, K.; Chatani, N.; Kurosawa, H.; Kawasaki, Y.; Murai, S. Organometallics 1990, 9, 3021.
25. 2Si derivative was sluggish. This is due presumably to the steric effect associated with silyl migration. For recent examples of steric effects of substituents at silicon on anionic migration, see: Marumoto, S.; Kuwajima, I. J. Am. Chem. Soc. 1993, 115, 9021.
26. We have confirmed that CO pressures (5-10 atm) can assist the reaction. Cf.: An equilibrium is suggested in the addition of organolithiums to isonitriles, isoelectronic compounds of CO. See: Niznik, G. E.; Morrison, W. H., III; Warborsky, H. M. J. Org. Chem. 1974, 39, 600. A reviewer pointed out that CO, considered as a "small electrophile," could react with a kinetic preference at the α-position. For an argument for regioselectivity based on steric factors associated with ethylene oxide, see ref 3d.