Stereoselective synthesis of furans by the Pd-catalyzed Oshima-Utimoto reaction

Organic Letters

Volumn 7, Issue 15, 2005, Pages 3367-3370

  Evans, Michael A ^a   Morken, James P ^a  

^a University of North Carolina at Chapel Hill   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; FURANS; MOLECULAR STRUCTURE; PALLADIUM; STEREOISOMERISM;

EID: 23044462967     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051275s     Document Type: Article

References (18)

1. Fraga, B. Nat. Prod. Rep. 2004, 21, 669.
2. For examples, see the following review: Koch, S. S. C.; Chamberlin, A. R. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier Science B. V.: Amsterdam, The Netherlands, 1995; Vol. 16, pp 687-725.
3. (a) Fugami, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1987, 28, 809.
4. (b) Fugami, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1989, 62, 2050.
5. For a related palladium-catalyzed dimerization of allyl alcohol, see: (c) Hafner, W.; Prigge, H.; Smidt, J. Liebigs Ann. Chem. 1966, 109.
6. For application of a related process to the synthesis of mycalamide A. see: (d) Sohn, J. E.; Waizumi, N.; Zhong, H. M.; Rawal, V. H. J. Am. Chem. Soc. 2005, ASAP.
7. For palladium-catalyzed syntheses of cyclic ethers, see: Hosokawa, T.; Murahashi, S.-I. Heterocycles 1992, 33, 1079.
8. (a) Larock, R. C.; Lee, N. H. J. Am. Chem. Soc. 1991, 113, 7815.
9. (b) Larock, R. C.; Stinn, D. E. Tetrahedron Lett. 1989, 30, 2767.
10. See also: (c) Kraus, G. A.; Thurston, J. J. Am. Chem. Soc. 1989, 111, 9203.
11. Grennenberg, H.; Gogoll, A.; Bäckvall, J. E. Organometallics 1993, 12, 1790.
12. Keul, H.; Choi, H.-S.; Kuczkowski, R. L. J. Org. Chem. 1985, 50, 3365.
13. For Pd-catalyzed isomerization of vinyl ethers, see: McKeon, J. E.; Fitton, P. Tetrahedron 1972, 28, 233.
14. For IR characterization of a Pd - olefin complex derived from a vinyl ether and palladium acetate, see: Wakatsuki, Y.; Nozakura, S. I.; Murahashi, S. Bull. Chem. Soc. Jpn. 1972, 45, 3426.
15. An oxonium ion related to 7 has been postulated previously: (a) Henry, P. M. J. Am. Chem. Soc. 1972, 94, 7316.
16. For a related iminium ion which appears to be involved in indole arylation, see: (b) Lane, B. S.; Brown, M. A.; Sames, D. J. Am. Chem. Soc. 2005, 127, ASAP.
17. Olah, G. A.; DeMember, J. R.; Mo, Y. K.; Svoboda, J. J.; Schilling, P.; Olah, J. A. J. Am. Chem. Soc. 1974, 96, 884.
18. C are broadened, indicating a fluxional process. The resonances for unreacted ethyl vinyl ether are unperturbed, suggesting the equilibrium transformation involving 6 includes a separate species. For a similar equilibrium process involving pyridine addition to a Pd(II) vinyl ether complex, see ref 9.