Samarium Barbier reactions of α-iodomethyloxazoles and thiazoles with aliphatic aldehydes

Organic Letters

Volumn 7, Issue 19, 2005, Pages 4099-4102

  Williams, David R ^a   Berliner, Martin A ^a   Stroup, Bryan W ^a   Nag, Partha P ^a   Clark, Michael P ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; FUSED HETEROCYCLIC RINGS; IODINE; OXAZOLE DERIVATIVE; SAMARIUM; THIAZOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; METHYLATION; SYNTHESIS;

ALDEHYDES; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; IODINE; METHYLATION; MOLECULAR STRUCTURE; OXAZOLES; SAMARIUM; THIAZOLES;

EID: 25444502128     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051345v     Document Type: Article

References (17)

1. For an overview, see: Kagan, H. B. Tetrahedron 2003, 59, 10351.
2. (a) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307.
3. (b) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321.
4. Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745.
5. Steel, P. G. J. Chem. Soc., Perkin Trans. 1 2001, 2727.
6. Berndt, M.; Gross, S.; Hölemann, A.; Reissig, H.-U. Synlett 2004, 422.
7. Williams, D. R.; Kiryanov, A. A.; Emde, U.; Clark, M. P.; Berliner, M. A. Angew. Chem., Int. Ed. 2003, 42, 1258.
8. Meyers, A. I.; Lawson, J. P. Tetrahedron Lett. 1981, 22, 3163.
9. Evans, D. A.; Cee, V. J.; Smith, T. E.; Santiago, K. J. Org. Lett. 1999, 1, 87.
10. Helquist, P.; Gangloff, A. R.; Akermark, B. J. Org. Chem. 1992, 57, 4797.
11. Uguen, D.; Breuilles, P. Tetrahedron Lett. 1998, 39, 3149.
12. Nonracemic 6 was prepared according to the method of Carreira: Carreira, E. M.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 12360.
13. (a) Tidwell, T. T. Synthesis 1990, 857.
14. (b) Mancuso, A. J.; Huang, S.-L.; Swern, D. J. Org. Chem. 1978, 43, 2480.
15. Haumann-Gaudinet, B.; Namy, J.-L.; Kagan, H. B. Tetrahedron Lett. 1997, 38, 6585.
16. Machrouhi, F.; Harmann, B.; Namy, J.-L.; Kagan, H. B. Synlett 1996, 633.
17. Aoyagi, Y.; Yoshimura, M.; Tsuda, M.; Tsuchibuchi, T.; Kawamata, S.; Tateno, H.; Asano, K.; Nakamura, H.; Obokata, M.; Ophta, A.; Kodama, Y. J. Chem. Soc., Perkin Trans. 1 1995, 689.