Highly Stereoselective Synthesis of trans-3-Aryl-4-carbethoxy-2,3-dihydro-2-fur-2′-oyl-5-methylfurans
Hui Zhang
Department of Chemistry, Shanghai University, Shanghai 200444, China
Search for more papers by this authorWei-Guo Cao
Department of Chemistry, Shanghai University, Shanghai 200444, China
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorJie Chen
Department of Chemistry, Shanghai University, Shanghai 200444, China
Search for more papers by this authorJi-Rong Hu
Department of Chemistry, Shanghai University, Shanghai 200444, China
Search for more papers by this authorJia-Xian Qian
Search for more papers by this authorShi-Zheng Zhu
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorHui Zhang
Department of Chemistry, Shanghai University, Shanghai 200444, China
Search for more papers by this authorWei-Guo Cao
Department of Chemistry, Shanghai University, Shanghai 200444, China
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorJie Chen
Department of Chemistry, Shanghai University, Shanghai 200444, China
Search for more papers by this authorJi-Rong Hu
Department of Chemistry, Shanghai University, Shanghai 200444, China
Search for more papers by this authorJia-Xian Qian
Search for more papers by this authorShi-Zheng Zhu
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorAbstract
Multi-substituted dihydrofurans are valuable intermediates for the synthesis of natural products and pharmaceuticals. Considerable attention has been focused on the development of efficient and regioselective methods for their preparation. Using K2CO3 as a base, with the reaction of fur-2-oylmethyltriphenylarsonium bromide 1 and ethyl 2-acetyl-3-arylacrylate 2 in tetrahydrofuran at room temperature, we found an efficient protocol was achieved to synthesize trans-3-aryl-4-carbethoxy-2,3-dihydro-2-fur-2′-oyl-5-methylfurans 3 in good yield with high stereoselectivity. The structure of compound 3 was confirmed by IR, 1H NMR, MS and HRMS. The mechanism for the formation of 3 was proposed.
REFERENCES
- 1 El-Shazly, R. M.; Al-Hazmi, G. A. A.; Ghazy, S. E.; El-Shahawi, M. S.; El-Asmy, A. A.. Spectrochim. Acta Part A, 2005, 61, 243.
- 2a Nakanishi, K., Natural Products Chemistry, Kod ansha Ltd., Academic, New York, 1974.
- 2b Meyers, A. I., Heterocycles in Organic Synthesis, John Wiley & Sons, New York, 1974.
- 2c Dean, F. M., In Advances in Heterocyclic Chemistry, Vol. 30, Ed.: A. R. Katritzky, Academic, New York, 1982, pp. 167–238.
- 2d Dean, F. M.; Sargent, M. V., In Comprehensive Heterocyclic Chemistry, Vol. 4, Eds.: C. W. Bird; G. W. H. Cheeseman, Pergamon, New York, 1984, Part 3, pp. 531–598.
- 2e Vernin, G., The Chemistry of Heterocyclic Flavoring and Aroma Compounds, Ellis Horwood, Chichester, 1982.
- 2f Danheiser, R. L.; Stoner, E. J.; Kojama, H.; Yamashita, D. S.; Klade, C. A.. J. Am. Chem. Soc., 1989, 111, 4407.
- 2g Fraga, B. M.. Nat. Prod. Rep., 1992, 9, 217.
- 2h Merrit, A. T.; Ley, S. V.. Nat. Prod. Rep., 1992, 9, 243.
- 3a Aso, M.; Ojida, A.; Yang, G.; Cha, O. J.; Osawa, E.; Kamematsu, K.. J. Org. Chem., 1993, 58, 3960.
- 3b Antonioletti, R.; Righi, G.; Oliveri, L.; Bovicelli, P.. Tetrahedron Lett., 2000, 41, 10127.
- 3c Antonioletti, R.; Bovicelli, P.; Malancona, S.. Tetrahedron, 2002, 58, 589.
- 3d Lee, Y. R.; Suk, J. Y.. Tetrahedron, 2002, 58, 2359.
- 4a Ichikawa, K.; Uemura, S.. J. Org. Chem., 1967, 32, 493.
- 4b Nishino, I.. Bull. Chem. Soc. Jpn., 1985, 58, 1922.
- 4c Yoshida, J.; Yano, S.; Ozawa, T.; Kawabata, N.. J. Org. Chem., 1985, 50, 3467.
- 4d Vinogradov, M. G.; Kondorsky, A. E.; Nikishin, G. I.. Synthesis, 1988, 60.
- 4e Tategami, S.; Yamada, T.; Nishino, H.; Korp, J. D.; Kurosawa, K.. Tetrahedron Lett., 1990, 31, 6371.
- 4f Iqbal, J.; Bhatia, B.; Nayyar, N. K.. Tetrahedron, 1991, 47, 6457.
- 4g Baciocchi, E.; Ruzziconi, R.. J. Org. Chem., 1991, 56, 4772.
- 4h Yamada, T.; Iwahara, Y.; Nishino, H.; Korp, J. D.; Kurosawa, K.. J. Chem. Soc., Perkin Trans. 1, 1993, 609.
- 4i McDonald, F. E.; Connolly, C. B.; Gleason, M. M.; Towne, T. B.; Treiber, K. D.. J. Org. Chem., 1993, 58, 6952.
- 4j Nair, V.; Mathew, J.; Radhakrishnan, K. V.. J. Chem. Soc., Perkin Trans. 1, 1996, 1487.
- 4k Roy, S. C.; Mandal, P. K.. Tetrahedron, 1996, 52, 2193.
- 4l Nguyen, V. H.; Nishino, H.; Kurosawa, K.. Synthesis, 1997, 899.
- 4m Alonso, I.; Carretero, J. C.; Garrido, J. L.; Magro, V.; Pedregal, C.. J. Org. Chem., 1997, 62, 5682.
- 4n Garrido, J. L.; Alonso, I.; Carretero, J. C.. J. Org. Chem., 1998, 63, 9406.
- 4o Garzino, F.; Meou, A.; Brun, P.. Tetrahedron Lett., 2000, 41, 9803.
- 4p Lee, Y. R.; Kim, B. S.; Kim, D. H.. Tetrahedron, 2000, 56, 8845.
- 4q Evans, D. A.; Sweeney, Z. K.; Rovis, T.; Tedrow, J. S.. J. Am. Chem. Soc., 2001, 123, 12095.
- 4r Zhang, Y.; Raines, A. J.; Flowers, R. A.II.. Org. Lett., 2003, 13, 2363.
- 5a Lee, P. H.; Kim, J. S.; Kim, S.. Tetrahedron Lett., 1993, 34, 7583.
- 5b Nakajima, T.; Segi, M.; Mituoka, T.; Fukute, Y.; Honda, M.; Naitou, K.. Tetrahedron Lett., 1995, 36, 1667.
- 5c Pohmakotr, M.; Takampon, A.; Ratchataphusit, J.. Tetrahedron., 1996, 52, 7149.
- 5d Yadav, V. K.; Balamurugan, R.. Org. Lett., 2001, 3, 2717.
- 5e Bernard, A. M.; Frongia, A.; Pier P. Piras, P.; Secci, F.; Spiga, M.. Org. Lett., 2005, 7, 4565.
- 5f Honda, M.; Naitou, T.; Hoshino, H.; Takagi, S.; Segi, M.; Nakajima, T.. Tetrahedron Lett., 2005 46, 7345.
- 6For less recent examples of synthesis of dihydrofurans using cyclopropanes or with involvement of cyclopropanes, see:
- 6a Alonso, M. E.; Morales, A.. J. Org. Chem., 1980, 45, 4530.
- 6b Saigo, K.; Kurihara, H.; Miura, H.; Hongu, A.; Kubota, N.; Nohira, H.; Hasegawa, M.. Synth. Commun., 1984, 14, 787.
- 6c Melot, J. M.; Texier-Boullet, F.; Foucaud, A.. Tetrahedron, 1988, 44, 2215.
- 7 Calò, V.; Scordari, F.; Nacci, A.; Schingaro, E.; D'Accolti, L.; Monopoli, A.. J. Org. Chem., 2003, 68, 4406.
- 8 Xing, C.; Zhu, S.. J. Org. Chem., 2004, 69, 6486.
- 9 Jiang, Y. I.; Ma, D.. Tetrahedron: Asymmetry, 2002, 13, 1033.
- 10 Arai, S.; Nakayama, K.; Suzuki, Y.; Hatano, K.; Shioiri, T.. Tetrahedron Lett., 1998, 39, 9739 and literatures therein for dihydrofuran formation as undesired or minor process in cyclopropanation reaction.
- 11a Cao, W.; Erden, I.; Keeffe, J. R.. Angew. Chem., Int. Ed. Engl., 1995, 1091.
- 11b Cao, W.; Ding, W.; Tong, W.; Liu, X.; Qiu, M.. Chem. J. Chin. Univ., 2000, 21, 740 (in Chinese).
- 11c Chen, Y; Ding, W.; Cao, W.; Lu, C.. Synth. Commun., 2001, 31, 3107.
- 11d Chen, Y.; Ding, W.; Cao, W.; Lu, C.. Chin. J. Chem., 2001, 19, 901.
- 11e Chen, Y.; Ding, W.; Cao, W.; Lu, C.. Synth. Commum., 2002, 32, 1953.
- 11f Ren, Z.; Ding, W.; Cao, W.; Wang, S.; Huang, Z.. Synth. Commum., 2002, 32, 3143.
- 11g
Yuan, M.;
Chen, Y.;
Ding, W.;
Cao, W..
Chin. J. Org. Chem.,
2003,
23,
901 (in Chinese).
10.1021/jo020421u Google Scholar
- 11h Cao, W.; Ding, W.; Chen, J.; Chen, Y.; Zang, Q.; Chen, G.. Synth. Commun., 2004, 34, 1599.
- 11i Ren, Z.; Cao, W.; Ding, W.; Wang, Y.; Wang, L.. Synth. Commun., 2004, 34, 3785.
- 11j Chen, G.; Cao, W.; Chen, J.; Chen, R.. Synth. Commun., 2004, 34, 3793.
- 11k Chen, Y.; Cao, W.; Ding, W.; Sun, X.. Chin. J. Chem., 2005, 23, 81.
- 11l Ren, Z.; Cao, W.; Tong, W.; Zhu, J.. Synth. Commun., 2005, 35, 2509.
- 11m Ren, Z.; Cao, W.; Chen, J.; Wang, Y.; Ding, W.. Synth. Commun., 2005, 35, 3099.
- 11n Zhou, X.; Cao, W.; Ren, Z.; Chen, J.; Zhang, H.. Chin. J. Synth. Chem., 2006, 14, 139 (in Chinese).
- 11o Ren, Z.; Cao, W.; Chen, J.; Wang, Y.; Ding, W.. J. Heterocycl. Chem., 2006, 43, 495.
- 12 Hagiwara, H.; Sato, K.; Nishino, D.; Hoshi, T.; Suzuki, T.; Ando, M.. J. Chem. Soc., Perkin Trans. 1, 2001, 2946.
- 13 Eistert, B.; Geiss, F.. Chem. Ber., 1961, 94, 929.
- 14 Ding, W.; Chen, Y.; Zhang, Y.; Yao, Y.. Chem. Res. Chin. Univ., 1996, 12, 354.
