Reaction of cis-2,3-bis(trimethylsilyl)cyclopropanone with β- ketophosphorus ylides: Unexpected formation of furans

Tetrahedron Letters

Volumn 41, Issue 18, 2000, Pages 3399-3402

  Takanami, Toshikatsu ^a   Ogawa, Atsuyo ^a   Suda, Kohji ^a  

^a MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

ketophosphorus ylide; 1,5 sigmatropic rearrangement; Cis 2,3 bis(trimethylsilyl)cyclopropanone; Cyclopropanone; Furan; Wittig olefination

Indexed keywords

CYCLOPROPANE DERIVATIVE; FURAN DERIVATIVE; KETONE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS;

EID: 0034728946     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00376-2     Document Type: Article

References (22)

1. For a review, see: Wasserman, H. H.; Berahl, D. R.; Lu, T. J. In The Chemistry of Cyclopropyl Group; Rappoport, Z., Ed.; John Wiley & Sons: New York, 1987; Part 2, p. 1455.
2. Matlin, A. R.; Lahti, P. M.; Appella, D.; Straumanis, A.; Lin, S.; Patel, H.; Jin, K.; Schrieber, K. P.; Pauls, J.; Raulerson, P. J. Am. Chem. Soc. 1999, 121, 2164; Hess Jr., B. A.; Eckart, U.; Fabian, J. J. Am. Chem. Soc. 1998, 120, 12 310; Sorensen, T. S.; Sun, F. Can. J. Chem. 1997, 75, 1030; Hrovat, D. A.; Rauk, A.; Sorensen, T. S.; Powell, H. K.; Borden, W. T. J. Am. Chem. Soc. 1996, 118, 4159; Sorensen, T. S.; Sun, F. J. Am. Chem. Soc. 1995, 117, 5592; Lim, D.; Hrovat, D. A.; Borden, W. T.; Jorgensen, W. L. J. Am. Chem. Soc. 1994, 116, 3494, and references cited therein.
3. Matlin, A. R.; Lahti, P. M.; Appella, D.; Straumanis, A.; Lin, S.; Patel, H.; Jin, K.; Schrieber, K. P.; Pauls, J.; Raulerson, P. J. Am. Chem. Soc. 1999, 121, 2164; Hess Jr., B. A.; Eckart, U.; Fabian, J. J. Am. Chem. Soc. 1998, 120, 12 310; Sorensen, T. S.; Sun, F. Can. J. Chem. 1997, 75, 1030; Hrovat, D. A.; Rauk, A.; Sorensen, T. S.; Powell, H. K.; Borden, W. T. J. Am. Chem. Soc. 1996, 118, 4159; Sorensen, T. S.; Sun, F. J. Am. Chem. Soc. 1995, 117, 5592; Lim, D.; Hrovat, D. A.; Borden, W. T.; Jorgensen, W. L. J. Am. Chem. Soc. 1994, 116, 3494, and references cited therein.
4. Matlin, A. R.; Lahti, P. M.; Appella, D.; Straumanis, A.; Lin, S.; Patel, H.; Jin, K.; Schrieber, K. P.; Pauls, J.; Raulerson, P. J. Am. Chem. Soc. 1999, 121, 2164; Hess Jr., B. A.; Eckart, U.; Fabian, J. J. Am. Chem. Soc. 1998, 120, 12 310; Sorensen, T. S.; Sun, F. Can. J. Chem. 1997, 75, 1030; Hrovat, D. A.; Rauk, A.; Sorensen, T. S.; Powell, H. K.; Borden, W. T. J. Am. Chem. Soc. 1996, 118, 4159; Sorensen, T. S.; Sun, F. J. Am. Chem. Soc. 1995, 117, 5592; Lim, D.; Hrovat, D. A.; Borden, W. T.; Jorgensen, W. L. J. Am. Chem. Soc. 1994, 116, 3494, and references cited therein.
5. Matlin, A. R.; Lahti, P. M.; Appella, D.; Straumanis, A.; Lin, S.; Patel, H.; Jin, K.; Schrieber, K. P.; Pauls, J.; Raulerson, P. J. Am. Chem. Soc. 1999, 121, 2164; Hess Jr., B. A.; Eckart, U.; Fabian, J. J. Am. Chem. Soc. 1998, 120, 12 310; Sorensen, T. S.; Sun, F. Can. J. Chem. 1997, 75, 1030; Hrovat, D. A.; Rauk, A.; Sorensen, T. S.; Powell, H. K.; Borden, W. T. J. Am. Chem. Soc. 1996, 118, 4159; Sorensen, T. S.; Sun, F. J. Am. Chem. Soc. 1995, 117, 5592; Lim, D.; Hrovat, D. A.; Borden, W. T.; Jorgensen, W. L. J. Am. Chem. Soc. 1994, 116, 3494, and references cited therein.
6. Matlin, A. R.; Lahti, P. M.; Appella, D.; Straumanis, A.; Lin, S.; Patel, H.; Jin, K.; Schrieber, K. P.; Pauls, J.; Raulerson, P. J. Am. Chem. Soc. 1999, 121, 2164; Hess Jr., B. A.; Eckart, U.; Fabian, J. J. Am. Chem. Soc. 1998, 120, 12 310; Sorensen, T. S.; Sun, F. Can. J. Chem. 1997, 75, 1030; Hrovat, D. A.; Rauk, A.; Sorensen, T. S.; Powell, H. K.; Borden, W. T. J. Am. Chem. Soc. 1996, 118, 4159; Sorensen, T. S.; Sun, F. J. Am. Chem. Soc. 1995, 117, 5592; Lim, D.; Hrovat, D. A.; Borden, W. T.; Jorgensen, W. L. J. Am. Chem. Soc. 1994, 116, 3494, and references cited therein.
7. Matlin, A. R.; Lahti, P. M.; Appella, D.; Straumanis, A.; Lin, S.; Patel, H.; Jin, K.; Schrieber, K. P.; Pauls, J.; Raulerson, P. J. Am. Chem. Soc. 1999, 121, 2164; Hess Jr., B. A.; Eckart, U.; Fabian, J. J. Am. Chem. Soc. 1998, 120, 12 310; Sorensen, T. S.; Sun, F. Can. J. Chem. 1997, 75, 1030; Hrovat, D. A.; Rauk, A.; Sorensen, T. S.; Powell, H. K.; Borden, W. T. J. Am. Chem. Soc. 1996, 118, 4159; Sorensen, T. S.; Sun, F. J. Am. Chem. Soc. 1995, 117, 5592; Lim, D.; Hrovat, D. A.; Borden, W. T.; Jorgensen, W. L. J. Am. Chem. Soc. 1994, 116, 3494, and references cited therein.
8. Wasserman and co-workers have reported that β-lactams can be prepared by the nitrogen-inserting ring expansion of cyclopropanones: J. Am. Chem. Soc. 1971, 93, 5586; Wasserman, H. H.; Baird, M. S. Tetrahedron Lett. 1971, 3721; Wasserman, H. H.; Cochoy, R. C.; Baird, M. S. J. Am. Chem. Soc. 1969, 91, 2375.
9. Wasserman and co-workers have reported that β-lactams can be prepared by the nitrogen-inserting ring expansion of cyclopropanones: J. Am. Chem. Soc. 1971, 93, 5586; Wasserman, H. H.; Baird, M. S. Tetrahedron Lett. 1971, 3721; Wasserman, H. H.; Cochoy, R. C.; Baird, M. S. J. Am. Chem. Soc. 1969, 91, 2375.
10. Wasserman and co-workers have reported that β-lactams can be prepared by the nitrogen-inserting ring expansion of cyclopropanones: J. Am. Chem. Soc. 1971, 93, 5586; Wasserman, H. H.; Baird, M. S. Tetrahedron Lett. 1971, 3721; Wasserman, H. H.; Cochoy, R. C.; Baird, M. S. J. Am. Chem. Soc. 1969, 91, 2375.
11. It is well known that cyclopropanone hemiacetals are useful three-carbon fragments in organic synthesis: Salaün, J. R. Y. In Small Ring Compounds in Organic Synthesis III; Meijere, A., Ed.; Springer-Verlag: Berlin, 1988; p. 1; Kuwajima, I.; Nakamura, E. In Small Ring Compounds in Organic Synthesis IV; 1990, p. 1, and references cited therein.
12. It is well known that cyclopropanone hemiacetals are useful three-carbon fragments in organic synthesis: Salaün, J. R. Y. In Small Ring Compounds in Organic Synthesis III; Meijere, A., Ed.; Springer-Verlag: Berlin, 1988; p. 1; Kuwajima, I.; Nakamura, E. In Small Ring Compounds in Organic Synthesis IV; 1990, p. 1, and references cited therein.
13. Fedorenko, E. N.; Zaitseva, G. S.; Baukov, Y. I.; Lutsenko, I. F. Zh. Obshch. Khim. 1986, 56, 2431; Zaitseva, G. S.; Novikova, L. I.; Livantsova, L. I.; Kisin, A. V.; Baukov, Y. I. Zh. Obshch. Khim. 1990, 60, 1073.
14. Fedorenko, E. N.; Zaitseva, G. S.; Baukov, Y. I.; Lutsenko, I. F. Zh. Obshch. Khim. 1986, 56, 2431; Zaitseva, G. S.; Novikova, L. I.; Livantsova, L. I.; Kisin, A. V.; Baukov, Y. I. Zh. Obshch. Khim. 1990, 60, 1073.
15. We have previously reported that 1,3,4-tris(trimethylsilyl)-β-lactam can easily be prepared by the reaction of silylcyclopropanone 1 with trimethylsilylazide: Suda, K.; Hotoda, K.; Iemuro, F.; Takanami, T. J. Chem. Soc., Perkin Trans. 1 1993, 1553; Suda, K.; Hotoda, K.; Aoyagi, M.; Takanami, T. J. Chem. Soc., Perkin Trans. 1 1995, 1327.
16. We have previously reported that 1,3,4-tris(trimethylsilyl)-β-lactam can easily be prepared by the reaction of silylcyclopropanone 1 with trimethylsilylazide: Suda, K.; Hotoda, K.; Iemuro, F.; Takanami, T. J. Chem. Soc., Perkin Trans. 1 1993, 1553; Suda, K.; Hotoda, K.; Aoyagi, M.; Takanami, T. J. Chem. Soc., Perkin Trans. 1 1995, 1327.
17. 3) δ 6.94 (23/100H, s), 5.73 (23/100H, s), 5.71 (77/100H, s), 2.25 (231/100H, s), 2.23 (69/100H, s), 1.81 (154/100H, s), 1.70 (46/100H, s), 0.25 (693/100H, s), 0.01 (693/100H, s), 0.00 (207/100H, s).
18. 3) data of E-3e is as follows: δ 7.49-7.48 (2H, m), 7.47-7.36 (2H, m), 7.35-7.20 (2H, m), 6.93 (1H, d, J=16.2 Hz), 6.48 (1H, d, J=16.2 Hz), 6.10 (1H, s), 1.85 (2H, s), 0.31 (9H, s), 0.03 (9H, s).
19. Huet, F.; Lechevallier, A.; Conia, J. M. Tetrahedron Lett. 1977, 29, 2521.
20. For a review, see: Hou, X. L.; Cheung, H. Y.; Hon, T. Y.; Kwan, P. L.; Lo, T. H.; Tong, S. Y.; Wong, H. N. C. Tetrahedron 1998, 54, 1955.
21. Silyl-substituted furans are also a useful precursor for the preparation of multi-substituted furans: Keay, B. A. Chem. Soc. Rev. 1999, 28, 209.
22. 4NF in THF: Bures, E.; Spinazze, P. G.; Beese, G.; Hunt, I. R.; Rogers, C.; Keay, B. A. J. Org. Chem. 1997, 62, 8741.