Efficient method for the lactonization of ω-hydroxycarboxylic acids with di-2-thienyl carbonate by the promotion of catalytic amounts of DMAP and Hf(OTf)4

Chemistry Letters

Volumn 34, Issue 5, 2005, Pages 710-711

  Oohashi, Yoshiaki ^a   Fukumoto, Kentarou ^a   Mukaiyama, Teruaki ^a,b  

^a KITASATO INSTITUTE   (Japan)

^b KITASATO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 22244482748     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2005.710     Document Type: Article

References (17)

1. DCC: E. P. Boden and G. E. Keck, J. Org. Chem., 50, 2394 (1985).
2. 2,4,6-Trichlorobenzoyl chloride: J. Inanaga, K. Hirata, H. Saeki, T. Katsuki, and M. Yamaguchi, Bull. Chem. Soc. Jpn., 52, 1989 (1979).
3. 3P: E. J. Corey and K. C. Nicolaou, J. Am. Chem. Soc., 96, 5614 (1974).
4. 3N: T. Mukaiyama, M. Usui, and K. Saigo, Chem. Lett., 1976, 49.
5. 2-benzoic anhydride (MNBA): I. Shiina, M. Kubota, H. Oshiumi, and M. Hashizume, J. Org. Chem., 69, 1822 (2004).
6. 3P: T. Kurihara, Y. Nakajima, and O. Mitsunobu, Tetrahedron Lett., 28, 2455 (1976).
7. 4-(Trifluoromethyl)benzoic anhydride: I. Shiina, Tetrahedron, 60, 1587 (2004).
8. 3: K. Ishihara, M. Kubota, H. Kurihara, and H. Yamamoto, J. Org. Chem., 61, 4560 (1996).
9. K. Venkataraman and D. R. Wagle, Tetrahedron Lett., 21, 1893 (1980);
10. E. J. Corey and D. J. Brunelle, Tetrahedron Lett., 28, 3409 (1976);
11. J. Otera, T. Yano, Y. Himeno, and H. Nozaki, Tetrahedron Lett., 27, 4501 (1986).
12. C. A. Dvorak, W. D. Schmitz, D. J. Poon, D. C. Pryde, J. P. Lawson, R. A. Amos, and A. I. Meyers, Angew. Chem., Int. Ed., 39, 1664 (2000).
13. Y. Oohashi, K. Fukumoto, and T. Mukaiyama, Chem. Lett., 34, 72 (2005).
14. Y. Oohashi, K. Fukumoto, and T. Mukaiyama, Chem. Lett., 34, 190 (2005).
15. I. Shiina, Y. Fukuda, T. Ishii, H. Fujisawa, and T. Mukaiyama, Chem. Lett., 1998, 831;
16. I. Shiina, H. Fujisawa, T. Ishii, and Y. Fukuda, Heterocycles, 52, 1105 (2000).
17. 4 (13.7 mg, 0.0176 mmol) in toluene (78 mL) at 100°C for 5 h and then reaction mixture was stirred for 1 h. The resultant solution was cooled to room temperature and was evaporated the solvent. The mixture was diluted in ether and was added saturated aqueous sodium hydrogen carbonate under ice cooling. The mixture was extracted with ether, and the organic layer was washed with water and brine, dried over sodium sulfate. After filtration of the mixture and evaporation of the solvent, the crude product was purified by preparative thin layer chromatography to afford the corresponding lactone (30.0 mg, 86%).