An unusual palladium-catalyzed carbonylative cyclization of β-bromovinyl aldehydes leading to lactones

Tetrahedron Letters

Volumn 47, Issue 23, 2006, Pages 3835-3837

  Cho, Chan Sik ^a   Shim, Hyung Sup ^a  

^a Kyungpook National University   (South Korea)

Author keywords

Bromovinyl aldehydes; Carbon monoxide; Carbonylative cyclization; Lactones; Palladium catalyst

Indexed keywords

ALDEHYDE DERIVATIVE; CARBON MONOXIDE; LACTONE DERIVATIVE; PALLADIUM COMPLEX;

ARTICLE; CARBONYLATION; CATALYSIS; CATALYST; CYCLIZATION;

EID: 33646151609     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.03.184     Document Type: Article

References (25)

1. In: Negishi E. (Ed). Handbook of Organopalladium Chemistry for Organic Synthesis Vol. II (2002), Wiley, New York 2309-2712
2. Colquhoun H.M., Thompson D.J., and Twigg M.V. Carbonylation: Direct Synthesis of Carbonyl Compounds (1991), Plenum Press, New York p 173
3. Cho C.S., Lee J.W., Lee D.Y., Shim S.C., and Kim T.J. Chem. Commun. (1996) 2115
4. Cho C.S., Chu D.Y., Lee D.Y., Shim S.C., Kim T.-J., Lim W.T., and Heo N.H. Synth. Commun. 27 (1997) 4141
5. Cho C.S., Jiang L.H., and Shim S.C. Synth. Commun. 28 (1998) 849
6. Cho C.S., Jiang L.H., Lee D.Y., Shim S.C., Lee H.S., and Cho S.-D. J. Heterocycl. Chem. 34 (1997) 1371
7. Cho C.S., Jiang L.H., and Shim S.C. Synth. Commun. 29 (1999) 2695
8. Lee D.Y., Cho C.S., Jiang L.H., Wu X., and Shim S.C. Synth. Commun. 27 (1997) 3449
9. Cho C.S., Baek D.Y., and Shim S.C. J. Heterocycl. Chem. 36 (1999) 1101
10. Cho C.S., Lim D.K., Kim T.-J., and Shim S.C. J. Chem. Res. (S) (2002) 550
11. Cho C.S., Baek D.Y., Kim H.Y., Shim S.C., and Oh D.H. Synth. Commun. 30 (2000) 1139
12. Coates R.M., Senter P.D., and Baker W.R. J. Org. Chem. 47 (1982) 3597
13. Ray J.K., Haldar M.K., Gupta S., and Kar G.K. Tetrahedron 56 (2000) 909
14. Zhang Y., and Herndon J.W. Org. Lett. 5 (2003) 2043
15. Mal S.M., Ray D., and Ray J.K. Tetrahedron Lett. 45 (2004) 277
16. Cho C.S., Patel D.B., and Shim S.C. Tetrahedron 61 (2005) 9490
17. Ray D., Mal S.K., and Ray J.K. Synlett (2005) 2135
18. Some S., Dutta B., and Ray J.K. Tetrahedron Lett. 47 (2006) 1221
19. For our recent report on palladium catalysis:. Cho C.S., Lim D.K., Heo N.H., Kim T.-J., and Shim S.C. Chem. Commun. (2004) 104
20. Cho C.S., Lim D.K., Zhang J.Q., Kim T.-J., and Shim S.C. Tetrahedron Lett. 45 (2004) 5653
21. Cho C.S. J. Mol. Catal. A: Chem. 240 (2005) 55
22. Cho C.S. J. Organomet. Chem. 690 (2005) 4094
23. Crisp G.T., and Meyer A.G. J. Org. Chem. 57 (1992) 6972
24. 3).
25. About trans/cis = 1/10 mixture, which could not be separated by chromatography:. Knobloch K., Koch J., Keller M., and Eberbach W. Eur. J. Org. Chem. (2005) 2715