Rhodium-catalyzed domino silylformylation of enynes involving carbocyclization

Tetrahedron Letters

Volumn 40, Issue 25, 1999, Pages 4703-4706

  Fukuta, Yukimasa ^a   Matsuda, Isamu ^a   Itoh, Kenji ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Carbocyclization; Carbonylation; Rhodium catalyst; Silylrhodation

Indexed keywords

RHODIUM; SILANE;

ARTICLE; CATALYSIS; CONFORMATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033580969     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00849-7     Document Type: Article

References (17)

1. 1. a) Negishi, E.; Copéret, C.; Ma, S.; Liou, S.; Liu, F. Chem. Rev. 1996, 96, 365-393.
2. b) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662.
3. 2. a) Pauson, P. L. Tetrahedron 1985, 41, 5855-5860.
4. b) Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187-6188.
5. c) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762-3763.
6. d) Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249-250.
7. e) Jeong, N.; Lee, S.; Sung, B. K. Organometallics 1998, 17, 3642-3644, and references therein.
8. 3. a) Matsuda, I.; Ogiso, A.; Sato, S.; Izumi, Y. J. Am. Chem. Soc. 1989, 111, 2332-2333.
9. b) Matsuda, I.; Fukuta, Y.; Tsuchihashi, T.; Nagashima, H.; Itoh, K. Organometallics 1997, 16, 4327-4345.
10. c) Ojima, I.; Ingallina, P.; Donovan, R. J.; Clos, N. Organometallics 1991, 10, 38-41.
11. d) Ojima, I.; Donovan, R. J.; Eguchi, M.; Shay, W. R.; Ingallina, P.; Korda, A.; Zeng, Q. Tetrahedron 1993, 49, 5431-5444.
12. 4. Muraoka, T.; Matsuda, I.; Itoh, K. Tetrahedron Lett. 1998, 39, 7325-7328.
13. 5. a) Matsuda, I.; Ishibashi, H.; Ii, N. Tetrahedron Lett. 1995, 36, 241-244.
14. b) Ojima, I.; Zhu, J.; Vidal, E. S.; Kass, D. F. J. Am. Chem. Soc. 1998, 120, 6690-6697.
15. 13C NMR spectra, and formula presented gave satisfactory results of combustion analyses. It is confirmed by the observation of an appreciable NOE enhancement (≈ 6%) between two couples of the protons as shown in the figure that the stereochemistry resulted from syn addition in the silylrhodation step remains intact in 2.
16. 2PhSiH under CO has been fragmentarily reported. a) Ojima, I.; Donovan, R. J.; Shay, W. R. J. Am. Chem. Soc. 1992, 114, 6580-6582.
17. b) Ojima, I.; McCullagh, J. V.; Shay, W. R. J. Organomet. Chem. 1996, 527, 421-423.