A cyclocarbonylation for the synthesis of bicyclic 3-methylene-1- phthalimidoylbutyrolactams from allene-hydrazones mediated by Mo(CO)6

Synlett

Volumn , Issue 15, 2007, Pages 2439-2441

  Kim, Sang Hoon ^a   Eui, Soo Kang ^a   Yu, Chan Mo ^a  

^a Sungkyunkwan University   (South Korea)

Author keywords

Allenes; Carbonylation; Cyclizations; Hydrazones; Molybdenum

Indexed keywords

3 METHYLENE 1 PHTHALIMIDOYLBUTYROLACTAM; DICHLOROMETHANE; DIMETHYL SULFOXIDE; HYDRAZONE DERIVATIVE; LACTAM DERIVATIVE; MOLYBDENUM; MOLYBDENUM HEXACARBONYL; UNCLASSIFIED DRUG;

ARTICLE; CARBONYLATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; SYNTHESIS;

EID: 34948881130     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-985603     Document Type: Article

References (32)

1. (a) For general discussions, see: Transition Metals for Organic Synthesis, Vol. I; Beller, M.; Bolm, C., Eds.; Wiley-VCH: Weinheim, 2004.
2. (b) Transition Metals for Organic Synthesis, Vol. II; Beller, M.; Bolm, C., Eds.; Wiley-VCH: Weinheim, 2004.
3. (a) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. Chem. Rev. 1996, 96, 635.
4. (b) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
5. (c) Trost, B. M.; Toste, F. D.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067.
6. (d) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813.
7. For examples, see: (a) Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 3182.
8. (b) Kablaoui, N. M.; Hick, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 4424.
9. (c) Mandal, S. M.; Amin, S. R.; Crowe, W. E. J. Am. Chem. Soc. 2001, 123, 6457.
10. (d) Ogoshi, S.; Oka, M.; Kurosawa, H. J. Am. Chem. Soc. 2004, 126, 11802.
11. For reviews, see: (a) Zimmer, R.; Dinesh, C. U.; Nandann, E.; Khan, F. A. Chem. Rev. 2000, 100, 3067.
12. (b) Ma, S. In Handbook of Organopalladium Chemistry for Organic Synthesis, Vol. 1; Negishi, E., Ed.; Wiley: New York, 2002, 1491-1521.
13. (c) Trost, B. M. Acc. Chem. Res. 2002, 35, 695.
14. (d) Ma, S. Eur. J. Org. Chem. 2004, 1175.
15. Mandai, T. In Modern Allene Chemistry, Vol. 2; Krause, N.; Hashmi, A. S. K., Eds.; Wiley-VCH: Weinheim, 2004, 925-972.
16. (a) Yu, C.-M.; Youn, J.; Lee, M.-K. Org. Lett. 2005, 7, 3733.
17. (b) Yu, C.-M.; Hong, Y.-T.; Yoon, S.-K.; Lee, J. Synlett 2004, 1695.
18. (c) Yu, C.-M.; Hong, Y.-T.; Lee, J. J. Org. Chem. 2004, 69, 8506.
19. (a) Yu, C.-M.; Youn, J.; Jung, J. Angew. Chem. Int. Ed. 2006, 45, 1553.
20. (b) Yu, C.-M.; Youn, J.; Jung, H.-K. Bull. Korean Chem. Soc. 2006, 27, 463.
21. (c) Yu, C.-M.; Kim, C.; Kweon, J.-H. Chem. Commun. 2004, 2494.
22. (d) Kang, S.; Hong, Y.-T.; Lee, J.-H.; Kim, W.-Y.; Lee, I.; Yu, C.-M. Org. Lett. 2003, 5, 2813.
23. Kang, S.-K.; Kim, K.-J.; Hong, Y.-T. Angew. Chem. Int. Ed. 2002, 41, 1584.
24. For reviews, see: (a) Bloch, R. Chem. Rev. 1998, 98, 1407.
25. (b) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069.
26. (a) Morimoto, T.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 1999, 121, 1758.
27. (b) Chatani, N.; Morimoto, T.; Kamitani, A.; Fukumoto, S.; Murai, S. J. Orgnomet. Chem. 1999, 579, 177.
28. For cyclization mediated by Mo, see: (a) Adrio, J.; Carretero, J. C. J. Am. Chem. Soc. 2007, 129, 778.
29. (b) Brummond, K. M.; Curran, D. P.; Mitasev, B.; Fischer, S. J. Org. Chem. 2005, 70, 1745.
30. (c) Cao, H.; Van Ornui, S. G.; Deschamps, J.; Flippen-Anderson, J.; Laib, F.; Cook, J. M. J. Am. Chem. Soc. 2005, 127, 933.
31. The crystallographic data for the structure of 4b has been deposited at the Cambridge Crystallographic Data Centre (CCDC 645332).
32. 3): δ = 25.3, 29.9, 36.9, 41.3, 46.7, 54.2, 121.7, 124.1, 124.4, 124.4, 127.4, 127.7, 130.0, 130.0, 130.3, 133.9, 135.0, 135.2, 137.7, 144.2, 164.6, 165.4, 166.4.