Stereoselective synthesis of dihydrofurans under phase-transfer catalyzed conditions

Tetrahedron Letters

Volumn 39, Issue 52, 1998, Pages 9739-9742

  Arai, Shigeru ^a   Nakayama, Keiji ^a   Suzuki, Yukari ^a   Hatano, Kei ichiro ^a   Shioiri, Takayuki ^a  

^a NAGOYA CITY UNIVERSITY   (Japan)

Author keywords

Bicyclic heterocyclic compounds; Catalysts; Furaris; Phase transfer

Indexed keywords

2 CYCLOHEXENONE DERIVATIVE; FURAN DERIVATIVE; METHYL GROUP;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CYCLIZATION; PHASE TRANSITION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032564550     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02239-4     Document Type: Article

References (24)

1. 1. We have succeeded in the development of the highly stereoselective synthesis of cyclopropane rings, see Arai, S.; Nakayama, K.; Hatano, K.; Shioiri, T. J. Org. Chem. in press.
2. 2. Quite recently, we have established some useful asymmetric processes under chiral PTC conditions, see (a) Arai, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2145-2148.
3. (b) Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997-3000.
4. (c) Arai, S.; Tsuge, H.; Shioiri, T. Tetrahedron Lett. in press.
5. (d) Arai, S.; Ishida, T.; Shioiri, T. Tetrahedron Lett. in press.
6. (e) Arai, S.; Oku, M.; Miura, M.; Shioiri, T. Synlett in press.
7. 3. Dihydrofuran formation has been often recognized as undesired or minor processes during cyclopropanation or other reactions, see (a) Jaxa-Chamiec, A. A.; Sammes, P. G.; Kennewell, P. D. J. Chem. Soc. Perkin 1980, 170-175.
8. (b) Farina, F.; Maestro, M. C.; Martin, M. V.; Soria, M. L. Tetrahedron 1987, 43, 4007-4014.
9. (c) Moorhoff, C. M. Tetrahedron Lett. 1996, 37, 9349-9352. The possibility of dihydrofuran ring formation under PTC-catalyzed cyclopropanation is discussed, see
10. (d) McIntosh, J. M.; Khalil, H. Can. J. Chem. 1978, 56, 2134-2138. Other examples of the synthesis of oxygen heterocycles were previously reported, see
11. (e) Arnold, Z.; Kral, V. Synthesis, 1984, 974-976.
12. (f) Yakura, T.; Tsuda, T.; Matsumura, Y.; Yamada, S.; Ikeda, M. Synlett 1996, 985-986. Quite recently, successful results for the metal catalyzed or mediated construction of furan derivatives were reported, see
13. (g) Palucki, M.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 10333-10334.
14. (h) Hojo, M.; Aihara, H.; Hosomi, A. J. Am. Chem. Soc. 1996, 118, 3533-3534.
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17. 4. α-Haloenones were easily prepared according to the described procedures, see (a) Kotsuki, H.; Shimanouchi, T.; Ohshima, R.; Fujiwara, S. Tetrahedron 1998, 54, 2709-2722.
18. (b) Kowalski, C.; Weber, A. E.; Fields, K. W. J. Org. Chem. 1982, 47, 5088-5093.
19. 5. Treatment of the corresponding α-iodo or bromoenone under similar reaction conditions gave 3a in low yields. Furthermore, the cyclic haloenones described in Table 1 were found to be unstable in basic media and lead to slow decomposition.
20. 4. Removal of the solvent followed by flash column chromatography (silica gel, hexane:diethyl ether = 1:2) gave the desired product 3b (150.3 mg, 95%) as a pale yellow oil.
21. 7. The stereochemistry of the monocyclic dihydrofurans were determined by comparison with the literature data, see (a) Alonso, M. E.; Morales, A.; Chitty, A. W. J. Org. Chem. 1982, 47, 3747-3754.
22. (b) Alonso, M.E.; Jano, P.; Hernandez, M.; I.; Greenberg, R. S.; Wenkert, E. J. Org. Chem. 1983, 48, 3047-3050.
23. 8. Aoyama, T.; Sonoda, N.; Yamauchi, M.; Toriyama, K.; Anzai, M.; Ando, A.; Shioiri, T. Symlett 1998, 35-36. Available from Wako Pure Chemical Industries, Ltd., Japan.
24. 9. Miwa, K.; Aoyama, T.; Shioiri, T. Synlett 1994, 461-462.