Facile approach to 4-substituted 2(5H)-furanones

Journal of Organic Chemistry

Volumn 65, Issue 16, 2000, Pages 5034-5036

  Yao, Min Liang ^a   Deng, Min Zhi ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

FURANONE DERIVATIVE;

ARTICLE; REACTION ANALYSIS; SYNTHESIS;

EID: 0034637498     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000195t     Document Type: Article

References (51)

1. (a) Miao, S.-C.; Andersen, R. J. J. Org. Chem. 1991, 56, 6275.
2. (b) Wang, T.-Z.; Pinard, E.; Paquette, L. A. J. Am. Chem. Soc. 1996, 118, 1309.
3. (c) Paquette, L. A.; Ezquerra, J.; He, W. J. Org. Chem. 1995, 60, 1435.
4. (d) Takayama, H.; Kuwajima, T.; Kitajima, M.; Nonato, M. G.; Aimi, N. Heterocycles 1999, 50, 75.
5. (e) Rodriguez, A. D.; Shi, J.-G.; Huang, S.-D. J. Org. Chem. 1998, 63, 4425.
6. (f) Xu, L.-P.; Gou, D.; Liu, J.-S.; Zheng, J.-H.; Koike, K.; Jia, Z.-H.; Nikaido, T. Heterocycles 1999, 51, 605.
7. (a) Cerri, A.; Mauri, P.; Mauro, M.; Melloni, P. J. Heterocycl. Chem. 1993, 30, 1581.
8. (b) Tan, L.; Chen, C.-Y.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1998, 39, 3961.
9. (c) Vallat, J.-N.; Grossi, P.-J.: Boucherie, A.; Simiand, J. Eur. J. Med. Chem. 1981, 16, 409.
10. (a) Brima, T. S. U. S.US 4,968, 817 US Appl. 635,338, 1984; Chem. Abstr. 1991, 114, 185246.
11. (a) Brima, T. S. U. S.US 4,968, 817 US Appl. 635,338, 1984; Chem. Abstr. 1991, 114, 185246.
12. (b) Tanabe, A. Jpn. Kokai Tokkyo Koho JP 63, 211, 276[88, 211, 276], 1988; Chem. Abstr. 1989, 110, 94978.
13. (b) Tanabe, A. Jpn. Kokai Tokkyo Koho JP 63, 211, 276[88, 211, 276], 1988; Chem. Abstr. 1989, 110, 94978.
14. (c) Ducharme, Y.; Gauthier, J. Y.; Prasit, P.; Leblanc, Y.; Wang, Z.; Leger, S.; Therien, M. PCT Int. Appl. WO 95 00, 501, 1995; Chem. Abstr. 1996, 124, 55954.
15. (c) Ducharme, Y.; Gauthier, J. Y.; Prasit, P.; Leblanc, Y.; Wang, Z.; Leger, S.; Therien, M. PCT Int. Appl. WO 95 00, 501, 1995; Chem. Abstr. 1996, 124, 55954.
16. Oomura, Y.; Shiraishi, T.; Takeoka, J. Jpn. Kokai Tokkyo Koho JP 07, 196, 491[95, 196, 491], 1995; Chem. Abstr. 1995, 123, 246850.
17. Oomura, Y.; Shiraishi, T.; Takeoka, J. Jpn. Kokai Tokkyo Koho JP 07, 196, 491[95, 196, 491], 1995; Chem. Abstr. 1995, 123, 246850.
18. Lattmann, E.; Hoffmann, H. M. R. Synthesis 1996, 155.
19. (a) For a recent review, see: Knight, D. W. Contemp. Org. Synth. 1994, 1, 287.
20. (b) Marshall, J. A.; Wolf, M. A. J. Org. Chem. 1996, 61, 3238.
21. (c) Xiao, W.-J.; Alper, H. J. Org. Chem. 1997, 62, 3422.
22. (d) Marshall, J. A.; Wolf, M. A. J. Org. Chem. 1997, 62, 367.
23. (e) Joh, T.; Nagata, H.; Takahashi, S. Inorg. Chim. Acta 1994, 220, 45.
24. (f) Forgione, P.; Wison, P. D.; Fallis, A. G. Tetrahedron Lett. 2000, 41, 17.
25. (a) Reginato, G.; Capperucci, A.; Degl'Innocenti, A.; Mordini, A.; Pecchi, S. Tetrahedron 1995, 51, 2129.
26. (b) Hoffmann, H. M. R.; Gerlach, K.; Lattmann, E. Synthesis 1996, 164.
27. (c) Hollingworth, G. J.; Sweeney, J. B. Tetrahedron 1992, 33, 7049.
28. (d) Hollingworth, G. J.; Perkins, G.; Sweeney, J. B. J. Chem. Soc., Perkin Trans. 1 1996, 1913.
29. (e) Maon, R,; Richecoeur, A. M. E.; Sweeney, J. B. J. Org. Chem. 1999, 64, 328.
30. (f) Ma, S.-M.; Shi, Z.-J. J. Org. Chem. 1998, 63, 6387.
31. (g) Boukouvalas, J.; Lachance, N.; Ouellet, M.; Trudeau, M. Tetrahedron Lett. 1998, 39, 7665.
32. (h) Ma, S.-M.; Shi, Z.-J.; Yu, Z.-Q. Tetrahedron Lett. 1999, 40, 2393.
33. (a) Piers, E.; Jean, M.; Marrs, P. S. Tetrahedron Lett. 1987, 28, 5075.
34. (b) Fouquet, E.; Pereyre, M.; Rodriguez, A. J. Org. Chem. 1997, 62, 5242.
35. For recent reviews, see: (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. and
36. (b) Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
37. (c) Ohe, T.; Miyaura, N.; Suzuki, A. J. Org. Chem. 1993, 58, 2201.
38. Grigg, R.; Kennewell, P.; Savic, V. Tetrahedron 1994, 50, 5489.
39. Honda, T.; Mizutani, H.; Kanai, K. J. Org. Chem. 1996, 61, 9374.
40. (a) Mullholland, T. P. C.; Foster, R.; Haydock, J. Chem. Soc., Perkin Trans. 1 1972, 1225.
41. (b) Greenhill, J. V.; Tomassini, T. Tetrahedron Lett. 1974, 2683.
42. (c) Schmidt, D. G.; Zimmer, H. Synth. Commun. 1981, 11, 385.
43. (a) Wang, X.-Z.; Deng, M.-Z. J. Chem. Soc., Perkin. Trans. 1 1996, 2663.
44. (b) Zhou, S.-M.; Yan, Y.-L.; Deng, M.-Z. Synlett 1998, 198.
45. (c) Ma, H.-R.; Wang, X.-H.; Deng, M.-Z. Synth. Commun. 1999, 29, 2477.
46. Yao, M.-L.; Deng, M.-Z. Synthesis accepted, 2000.
47. (a) Uenishi, J.; Beau, J.-M.; Armstrong, R. W.; Kishi, Y. J. Am. Chem. Soc. 1987, 109, 4156.
48. (b) Gillmann, T.; Weeber, T. Synlett 1994, 649.
49. (c) Gronowitz, S.; Björk, P.; Malm, J.; Hörnfeldt, A. B. J. Organomet. Chem. 1993, 460(1), 127.
50. (1R,2R)-2-Phenylcyclopropylboronic acid (1f) and (1S,2S)-2-phenylcyclopropyl-boronic acid (1g) were prepared via the asymmetricly cyclopropanation of trans-tosylboronic acid ester of (+)-TMTA and (-)-TMTA, respectively, according to our previous procedure (see: Zhou, S.-M.; Deng, M.-Z.; Xia, L.-J.; Tang, M.-H. Angew. Chem., Int. Ed. Engl. 1998, 37, 2845-2847.)
51. Delgado, J.; Espinós, A.; Jiménez, M. C.; Miranda, M. A.; Roth, H. D.; Tormos, R. J. Org. Chem. 1999, 64, 6541, and references therein.