An efficient synthesis of five-membered cyclic ethers from 1,3-diols using molecular iodine as a catalyst

Journal of Oleo Science

Volumn 57, Issue 8, 2008, Pages 437-443

  Kasashima, Yoshio ^a   Fujimoto, Hiroshi ^b   Mino, Takashi ^b   Sakamoto, Masami ^b   Fujita, Tsutomu ^b  

^a CHIBA INSTITUTE OF TECHNOLOGY   (Japan)

^b CHIBA UNIVERSITY   (Japan)

Author keywords

1,3 diol; Etherification; Five membered ether ring; Iodine

Indexed keywords

EID: 49249109117     PISSN: 13458957     EISSN: 13473352     Source Type: Journal    
DOI: 10.5650/jos.57.437     Document Type: Article

References (24)

1. Fujita, T.; Watanabe, S.; Tohtani, M.; Suga, K. A convenient preparation of γ-lactones and dialkyltetrahydrofurans from the reaction of fatty acids with epoxides using lithium naphthalenide. J. Am. Oil Chem. Soc. 61, 1604-1606 (1984).
2. Lukevics, E.; Gevorgyan, V.N.; Goldberg, Y.S.; Shymanska, M.V. Synthesis of 3-(2,5-dihydrofural)-silanes and - germanes and their transformations under catalytic hydrogenation conditions. J. Organometallic Chem. 263, 283-296 (1984).
3. Eames, J.; Warren, S. Kinetic and thermodynamic control in the stereospecific synthesis of cyclic ethers via phenylsulfanyl migration. Tetrahedron Lett. 37, 3525-3528 (1996).
4. Eames, J.; Heras, M.A.de las; Warren, S. Secondary and tertiary alcohols as nucleophiles in the stereospecific synthesis of substituted tetrahydrofurans by cyclization of 1,3-diols with phenylsulfanyl migration. Tetrahedron Lett. 37, 4077-4080 (1996).
5. Tamaru, Y.; Yoshida, Z. Heterocyclic synthesis by the use of the oxidizing potential of palladium(II). J. Organometallic Chem. 334, 213-223 (1987).
6. Kato, K.; Tanaka, M.; Yamamoto, Y.; Akita, H. Asymmetric cyclization-carbonylation of cyclic-2-mehtyl-2-propargyl-1,3-diols. Tetrahedron Lett. 43, 1511-1513 (2002).
7. Christlieb, M.; Davis, J.E.; Eames, J.; Hooley, R.; Warren, S. The stereoselective synthesis of oxetanes; Exploration of a new, Mitsunobu-style procedure for the cyclization of 1,3-diols. J. Chem. Soc., Perkin Trans. 1 2001, 2983-2996 (2001).
8. Gruttadauria, M.; Aprile, C.; Noto, R. Stereocontrolled approach to δ- and γ-lactones and 1,3-diols. The role of X- ion in the selenolactonization. Tetrahedron Lett. 43, 1669-1672 (2002).
9. Pavlinac, J.; Zupan, M.; Stavber, S. Effect of water on the functionalization of substituted anisoles with iodine in the presence of F-TEDA-BF4 or hydrogen peroxide. J. Org. Chem. 71, 1027-1032 (2006).
10. Wu, J.; Xia, H.; Gao, K. Molecular iodine: a highly efficient catalyst in the synthesis of quinoline via Friedlander annulation. Org. Biomol. Chem. 4, 126-129 (2006).
11. Das, B.; Rebby, K.R.; Ramu, R.; Thirupathi, P.; Ravikanth, B. Iodine as an efficient catalyst for one-pot multicomponent synthesis of β-axetamido ketones. Synth. Lett. 2006, 1756-1758 (2006).
12. Lin, X.; Cui, S.; Wang, Y. Molecular iodine-catalyzed one-pot synthesis of substituted quinolines from imines and aldehydes. Tetrahedron Lett. 47, 3127-3130 (2006).
13. Bosco, J.W.J.; Agrahari, A.; Saikia, A.K. Molecular iodine catalyzed selective acetylation of alcohols with acetate. Tetrahedron Lett. 47, 4065-4068 (2006).
14. Lin, X.; Cui, S.; Wang, Y. A highly efficient synthesis of 1,2,3,4-tetrahydroquinolines by molecular iodine-catalyzed domino reaction of anilines with cyclic enol ethers. Tetrahedron Lett. 47, 4509-4512 (2006).
15. Yadav, J.S.; Balanarsaiah, E.; Raghavendra, S.; Satyanarayana, M. Chemoselective hydrolysis of tert-butyl esters in acetonitrile using molecular iodine as a mild and efficient catalyst. Tetrahedron Lett. 47, 4921-4924 (2006).
16. Kidwai, M.; Mothsra, P. A one-pot synthesis of 1,2,4,5-tetraarylimidazoles using molecular iodine as an efficient catalyst. Tetrahedron Lett. 47, 5029-5031 (2006).
17. Kidwai, M.; Mothsra, P.; Bansal, V.; Somvanshi, R.K.; Ethayathulla, A.S.; Dey, S.; Singh, T.P. One-pot synthesis of highly substituted imidazoles using iodine: A versatile catalyst. J. Molecular Catalysis, A: Chemical 265, 177-182 (2007).
18. Kidwai, M.; Bansal, V.; Mothsra, P. Molecular iodine: A highly efficient catalyst for the synthesis of 7-arylbenzopyrano[1,3]diazepines in non-protic solvents. J. Molecular Catalysis, A: Chemical 266, 43-46 (2007).
19. Zmitek, K.; Zupan, M.; Stavber, S.; Iskra, J. The effect of iodine on the peroxidation of carbonyl compounds. J. Org. Chem. 72, 6534-6540 (2007).
20. Das, B.; Chowdhury, N.; Damodar, K. Iodine-catalyzed efficient conjugate addition of pyrroles to α,β-unsaturated ketones. Tetrahedron Lett. 48, 2867-2870 (2007).
21. Liu, Z.; Liu, L.; Shafiq Z.; Wu, Y.; Wang, D.; Chen, Y. Iodine-catalyzed allylation and propargylation of indoles with allylic and propargylic acetates, Tetrahedron Lett. 48, 3963-3967 (2007).
22. Kim, K.M.; Ryu, E.K. Unusual iodine catalyzed lactonization of γ-methyl-γ,δ-pentenoic acids: A facile synthesis of γ,γ-dimethyl-γ-butyrolactones. Tetrahedon Lett. 37, 1411 (1996).
23. Fujita, Y.; Hanyu, N.; Aoki, T.; Mino, T. Sakamoto, M. Iodine mediated lactonization of terpenic 3-hydroxy acids. Synthesis 2001, 1846 (2001).
24. 17O-NMR and electrospray ionization mass spectroscopy. Helvetica Chimica Acta 82, 1385-1399 (1999).