Montmorillonite K 10 (clay) catalyzed hydrolysis of aryl-substituted α,β-difluoroallyl alcohols leading to (Z)-α-fluoro-β-aryl-substituted acrylaldehydes

Tetrahedron

Volumn 55, Issue 15, 1999, Pages 4637-4642

  Funabiki, Kazumasa ^a   Murata, Eiji ^a   Fukushima, Yoshitaka ^a   Matsui, Masaki ^a   Shibata, Katsuyoshi ^a  

^a GIFU UNIVERSITY   (Japan)

Author keywords

Clays and earths; Enals; Fluorine and compounds; Hydrolysis; Stereoselection; Supported reagents reaction

Indexed keywords

ACRYLALDEHYDE; ALDEHYDE DERIVATIVE; ALLYL ALCOHOL; FLUORINE; MONTMORILLONITE; SEX PHEROMONE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CLAY; HYDROLYSIS; INSECT; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

INSECTA;

EID: 0033537955     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)80001-5     Document Type: Article

References (43)

1. Kikan Kagaku Sosetsu, Microporous Crystals, The Chemical Society of Japan, Tokyo, 1997; pp. 113-126.
2. Izumi, Y.; Urabe, K.; Onaka, M. Zeolite, Clay, and Heteropoly Acid in Organic Reactions, Kodansha Ltd, Tokyo, 1992; pp. 21-47.
3. Balogh, M. Organic Chemistry Using Clays, Springer-Verlag, New York, 1993.
4. Tateiwa, J.; Uemura, S. J. Jpn. Petrol. Inst. 1997, 40, 329-341.
5. Tateiwa, J.; Hashimoto, K.; Yamauchi, T.; Uemura, S. Bull. Chem. Soc. Jpn. 1996, 69, 2361-2368.
6. Prabahar, K. J.; Ferris, J. P. J. Am. Chem. Soc. 1997, 119, 4330-4337.
7. Ertem, G.; Ferris, J. P. J. Am. Chem. Soc. 1997, 119, 7197-7201.
8. Clark, J. H.; Ross, J. C.; Macquarrie, D. J.; Barlow, S. J.; Bastock, T. W. Chem. Commun. 1997, 1203-1204.
9. Li. A. -X.; Li, T. -S.; Ding, T. -H. Chem. Commun. 1997, 1389-1390.
10. Varma, R. S.; Dahiya, R.; Kumar, S. Tetrahedron Lett. 1997, 38, 2039-2042.
11. Kumar, H. M. S.; Reddy, B. V. S.; Mohanty, P. K.; Yadav, J. S. Tetrahedron Lett. 1997, 38, 3619-3622.
12. Venkatachalapathy, C.; Pitchumani, K. Tetrahedron 1997, 53, 2581-2584.
13. Arienti, A.; Bigi, F.; Maggi, R.; Marzi, E.; Moggi, P.; Rastelli, M.; Sartori, G.; Tarantola, F. Tetrahedron 1997, 53, 3795-3804.
14. Kannan, P.; Sevvel, R.; Rajagopal, S.; Pitchumani, K.; Srinivasan, C. Tetrahedron 1997, 53, 7635-7640.
15. Venkatachalapathy, C.; Pitchumani, K. Tetrahedron 1997, 53, 17171-17176.
16. Varma, R. S.; Saini, R. K. Synlett 1997, 857-858.
17. Kannan, P.; Pichumani, K. Catal. Lett. 1997, 45, 271-273.
18. Ponde, D. E.; Deshpande, V. H.; Bulbule, V. J.; Sudalai, A.; Gajare, A. S. J. Org. Chem. 1998, 63, 1058-1063.
19. Nishimura, T.; Onoue, T.; Ohe, K.; Tateiwa, J.; Uemura, S. Tetrahedron Lett. 1998, 39, 4359-4362.
20. Varma, R. S.; Dahiya, R.; Tetrahedron 1998, 54, 6293-6298.
21. Hirano, M.; Yakabe, S.; Monobe, H.; Morimoto, T. Synth. Commun. 1998, 28, 669-676.
22. Toshima, K.; Ushiki, Y.; Matsuo, G.; Matsumura, S. Tetrahedron Lett. 1997, 38, 7375-7378.
23. Tateiwa, J.; Kimura, A.; Takasuka, M.; Uemura. S. J. Chem. Soc., Perkin Trans. 1 1997, 2169-2179.
24. Mohan, J. M.; Uphade, B. S.; Choudhary, V. R.; Ravindranathan, T.; Sudalai, A. Chem. Commun. 1997, 1429-1430.
25. Avalos, M.; Babiano, R.; Bravo, J. L.; Cintas P.; Jiménez, J. L.; Palacios, J. C.; Ranu, B. C. Tetrahedron Lett. 1998, 39, 2013-2016.
26. Allmendinger, T.; Furet, P.; Hungerbühler, E. Tetrahedron Lett. 1990, 31, 7297-7300.
27. Allmendinger, T.; Felder, E.; Hungerbühler, E. Tetrahedron Lett. 1990, 31, 7301-7304.
28. Camps, F.; Coll, J.; Fabrias, G.; Guerrero, A. Tetrahedron 1984, 40, 2871-2878.
29. Daubresse, N.; Chupeau, Y.; Francesch, C.; Lapierre, C.; Pollet, B.; Rolando, C. Chem. Commun. 1997, 1489-1490.
30. Pirrung, M. C.; Rowley, E. G.; Holmes, C. P. J. Org. Chem. 1993, 58, 5683-5689.
31. Hibi, S.; Kikuchi, K.; Yoshimura, H.; Nagai, M.; Tai, K.; Hida, T. J. Med. Chem. 1998, 41, 3245-3252.
32. Our contribution to α-fluoro-β-alkyl or aryl-α,β-unsaturated aldehydes, see: Funabiki, K.; Kurita, T.; Matsui, M.; Shibata, K. Chem. Lett. 1997, 739-740.
33. Yamanaka, H.; Odani, Y.; Ishihara, T.; Gupton, J. T. Tetrahedron Lett. 1998, 39, 6943-6946.
34. Satoh, T.; Kitoh, Y.; Onda, K.; Takano, K.; Yamakawa, K. Tetrahedron 1994, 50, 4957-4972.
35. Tellier, F.; Sauvétre, R. J. Fluorine Chem. 1991, 51, 397-405.
36. Patrick, T. B.; Hosseini, S.; Bains, S. Tetrahedron Lett. 1990, 31, 179-182.
37. Sauvétre, R.; Masure, D.; Chuit, C.; Normant, J. F. Synthesis 1978, 128-130.
38. Bessière, Y.; Savary, D. N. -H.; Schlosser, M. Helv. Chim. Acta 1977, 60, 1739-1746.
39. Kimoto, H.; Muramatsu, H.; Inukai, K. Nippon Kagaku Kaishi 1975, 1926-1933.
40. A preliminary portion of this work has been published, see: Funabiki, K.; Fukushima, Y.; Inagaki, T.; Murata, E.; Matsui, M.; Shibata, K. Tetrahedron Lett. 1998, 39, 1913-1916.
41. Ookoshi, T.; Onaka, M. Tetrahedron Lett. 1998, 39, 293-296.
42. Funabiki, K.; Ohtsuki, T.; Ishihara, T.; Yamanaka, H. J. Chem. Soc., Perkin Trans. 1 1998, 2413-2423 and references cited therein.
43. Matsui, M.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1996, 69, 137-139.