The Ru3(CO)12-catalyzed intermolecular [2+2+1] cyclocoupling of imines, alkenes or alkynes, and carbon monoxide: A new synthesis of functionalized γ-lactams

Synthesis

Volumn , Issue 7, 2000, Pages 925-928

  Chatani, Naoto ^a   Tobisu, Mamoru ^a   Asaumi, Taku ^a   Murai, Shinji ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Carbon monoxide; Cycloaddition; Imines; Ruthenium carbonyl

Indexed keywords

2 PYRROLIDINONE; ALKENE; BETA LACTAM; CARBON MONOXIDE; ESTER; HETEROCYCLIC COMPOUND; IMINE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; MOLECULAR INTERACTION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0033938651     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2000-6295     Document Type: Article

References (16)

1. For reviews on transition-metal-catalyzed cycloaddition reactions, see: Schore, N. E. Chem. Rev. 1988, 88, 1081. Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
2. For reviews on transition-metal-catalyzed cycloaddition reactions, see: Schore, N. E. Chem. Rev. 1988, 88, 1081. Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
3. For reviews on transition-metal-catalyzed cycloaddition reactions, see: Schore, N. E. Chem. Rev. 1988, 88, 1081. Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
4. Chung, Y. K. Coord. Chem. Rev. 1999, 188, 297.
5. Crowe, W. E.; Vu, A. T. J. Am. Chem. Soc. 1996, 118, 1557.
6. Kablaouni, N. M.; Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 5818. Kablaouni, N. M.; Hicks, F. A.; Buchwald, S. L. J. Am. Chem Soc. 1997, 119, 4424.
7. Kablaouni, N. M.; Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 5818. Kablaouni, N. M.; Hicks, F. A.; Buchwald, S. L. J. Am. Chem Soc. 1997, 119, 4424.
8. Chatani, N.; Morimoto, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1998, 120, 5335.
9. Chatani, N.; Morimoto, T.; Kamitani, A.; Fukumoto, Y.; Murai, S. J. Organomet. Chem. 1999, 579, 177.
10. Chatani, N.; Tobisu, M.; Asaumi, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1999, 121, 7160.
11. Gamzu, E. R.; Hoover, T. M.; Gracon, S. I. Drug. Dev. Res. 1989, 18, 177; and references cited therein.
12. Tejero, T.; Dondoni, A.; Rojo, I.; Merchàn, F. L.; Merino, P. Tetrahedron 1997, 53, 3301.
13. Although the mechanism for the present catalytic reaction is not clear, a similar stoichiometric reaction has been reported. Feiken, N.; Schreuder, P.; Siebenlist, R.; Frühauf, H.-W.; Vrieze, K.; Kooijman, H.; Veldman, N.; Spek, A. L.; Fraanje, J.; Goubitz, K. Organometallics 1996, 15, 2148; and references cited therein.
14. A trace amount of the regioisomer of 7 was detected by GC.
15. Supporting information including typical experimental procedures and the details of spectral data of new compounds are available on request to the author by e-mail or fax.
16. Bruce, M. I.; Jensen, C. M.; Jones, N. L. Inorg. Synth. 1989, 26, 259.