Lewis acid-catalyzed conjugate addition-cyclization reactions of ethenetricarboxylates with substituted propargyl alcohols: Stereoselectivity in the efficient one-pot synthesis of methylenetetrahydrofurans

Journal of Organic Chemistry

Volumn 72, Issue 17, 2007, Pages 6459-6463

  Morikawa, Satoshi ^a,b   Yamazaki, Shoko ^a   Tsukada, Momoko ^a   Izuhara, Suguru ^a   Morimoto, Tsumoru ^b   Kakiuchi, Kiyomi ^b  

^a NARA UNIVERSITY OF EDUCATION   (Japan)

^b NARA INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIZED PRODUCTS; ETHENETRICARBOXYLATE DERIVATIVES; METHYLENETETRAHYDROFURANS; PROPARGYL ALCOHOLS;

ALCOHOLS; FURAN RESINS; MOLECULAR STRUCTURE; REACTION KINETICS; STEREOSELECTIVITY;

ESTERS;

ALCOHOL DERIVATIVE; ESTER; ETHENETRICARBOXYLATE DERIVATIVE; LEWIS ACID; METHYLENETETRAHYDROFURAN; SILICON; TETRAHYDROFURAN DERIVATIVE; TRICARBOXYLIC ACID; UNCLASSIFIED DRUG; ZINC BROMIDE;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CYCLIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HIGH TEMPERATURE; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

ACIDS; ALKYNES; CARBOXYLIC ACIDS; CATALYSIS; CYCLIZATION; FURANS; MAGNETIC RESONANCE SPECTROSCOPY; PROPANOLS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, INFRARED; STEREOISOMERISM;

EID: 34547947084     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070882l     Document Type: Article

References (51)

1. (a) Keay, B. A.; Dibble, P. W. In Comprehensive Heterocyclic Chemistry 11; Katrizky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, UK, 1996; Vol. 2, p 395.
2. (b) Donnelly, D. M. X.; Meegan, M. J. In Comprehensive Heterocyclic Chemistry I; Katrizky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, UK, 1984; Vol. 4, p 657.
3. For examples see: (a) Belting, V.; Krause, N. Org. Lett. 2006, 8, 4489.
4. (b) Wolfe, J. P.; Rossi, M. A. J. Am. Chem. Soc. 2004, 126, 1620.
5. (c) Alonso, F.; Meléndez, J.; Soler, T.; Yus, M. Tetrahedron 2006, 62, 2264.
6. (d) Sharma, G. V. M.; Kumara, K. R.; Sreenivasa, P.; Krishnaa, P. R.; Chorghadeb, M. S. Tetrahedron: Asymmetry 2002, 13, 687.
7. (e) Bassetti, M.; D'Annibale, A.; Fanfoni, A.; Minissi, F. Org. Lett. 2005, 7, 1805.
8. (f) Trost, B. M.; Machacek, M. R.; Faulk, B. D. J. Am. Chem. Soc. 2006, 128, 6745.
9. (g) Jahn, U.; Rudakov, D. Org. Lett. 2006, 8, 4481.
10. (h) Micalizio, G. C.; Roush, W. R. Org. Lett. 2000, 2, 461.
11. For a review see: (i) Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293.
12. (a) Marat, X.; Monteiro, N.; Balme, G. Synlett 1997, 845.
13. (b) Cavicchioli, M.; Marat, X.; Monteiro, N.; Hattmann, B.; Balme, G. Tetrahedron Lett. 2002, 43, 2609.
14. (c) Nakamura, M.; Liang, C.; Nakamura, E. Org. Lett. 2004, 6, 2015.
15. Yakura, T.; Yamada, S.; Shiima, M.; Iwamoto, M.; Ikeda, M. Chem. Pharm. Bull. 1998, 46, 744.
16. Morikawa, S.; Yamazaki, S.; Furusaki, Y.; Amano, N.; Zenke, K.; Kakiuchi, K. J. Org. Chem. 2006, 71, 3540-3544.
17. 2Cl gave a noncyclized adduct, triethyl 1-(prop-1-ynyloxy)ethane-1,2,2-tricarboxylate in 42-49% yield, along with starting material 1a (27-30%).
18. Igawa, K.; Tomooka, K. Angew. Chem., Int. Ed. 2006, 45, 232.
19. (a) Denmark, S. E.; Neuville, L.; Christy, M. E. L.; Tymonko, S. A. J. Org. Chem. 2006, 71, 8500.
20. (b) Denmark, S. E.; Choi, J. Y. J. Am. Chem. Soc. 1999, 121, 5821.
21. (c) Hirabayashi, K.; Ando, J.; Mori, A.; Nishihara, Y.; Hiyama, T. Synlett 1999, 99.
22. (d) Shibata, K.; Miyazawa, K.; Goto, Y. Chem. Commun. 1997, 1309.
23. (e) Gouda, K.-I.; Hagiwara, E.; Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1996, 61, 7232.
24. (f) Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1988, 53, 918.
25. (g) Denmark, S. E.; Tymonko, S. A. J. Am. Chem. Soc. 2005, 127, 8004.
26. (h) Trost, B. M.; Machacek, M. R.; Ball, Z. T. Org. Lett. 2003, 5, 1895.
27. (i) Anderson, J. C.; Munday, R. H. J. Org. Chem. 2004, 69, 8971.
28. (j) Babudri, F.; Farinola, G. M.; Naso, F.; Panessa, D. J. Org. Chem. 2000, 65, 1554.
29. (a) Earl, R. A.; Townsend, L. B. Can. J. Chem. 1980, 58, 2550.
30. (b) Earl, R. A.; Townsend, L. B. Organic Syntheses; Wiley: New York, 1990; Collect. Vol. VII, p 334.
31. (a) Piers, E.; Chong, J. M.; Morton, H. E. Tetrahedron 1989, 45, 363.
32. (b) Munt, S. P.; Thomas, E. J. J. Chem. Soc., Chem Commun. 1989, 480.
33. (c) Trost, B. M.; Frontier, A. J. J. Am. Chem. Soc. 2000, 122, 11727.
34. Tufariello, J. J.; Tette, J. P. J. Org. Chem. 1975, 40, 3866.
35. 4 chelete intermediate of 2,4-substitutents with esters in the tetrahydrofuran ring.
36. Possible isomerization of propargylic alcohols, such as via Meyer-Schuster and Rupe rearrangements, may occur in preference to the expected reaction with 1. (a) Bigi, F.; Carloni, S.; Maggi, R.; Muchetti, C.; Sartori, G. J. Org. Chem. 1997, 62, 7024.
37. (b) Luzung, M. R.; Tosle, F. D. J. Am Chem. Soc. 2003, 125, 15760.
38. (c) Zhao, W.; Carreira, E. M. Org. Lett. 2003, 5, 4153.
39. (d) Narasaka, K.; Kusama, H.; Hayashi, Y. Chem. Lett. 1991, 1413.
40. (e) Lorber, C. Y.; Osborn, J. A. Tetrahedron Lett. 1996, 37, 853.
41. (f) Chabardes, P. Tetrahedron Lett. 1988, 29, 6253.
42. For examples see: (a) Johnson, C. R.; Elliot, R. C.; Meanwell, N. A. Tetrahedron Lett.. 1982, 23, 5005.
43. (b) Jackson, R. F. W.; Raphael, R. A. Tetrahedron Lett. 1983, 24, 2117.
44. (c) Sakurai, K.; Takahashi, K.; Yoshida, T. Agric. Biol. Chem. 1983, 47, 1249.
45. (d) Kaiser, R. Helv. Chim. Acta 1984, 67, 1198.
46. (e) Hirasawa, Y.; Morita, H.; Shiro, M.; Kobayashi J. Org. Lett. 2003, 5, 3991.
47. (f) Trost, B. M.; Mao, M. K.-T.; Balkovec, J. M.; Buhlmayer, P. J. Am. Chem. Soc. 1986, 108, 4965.
48. (g) Uenishi, J.; Kawahama, R.; Yonemitsu, O. J. Org. Chem. 1997, 62, 1691.
49. 3N) attack leading to anionic zinc coordinate enolate-ester is suggested. The detailed reaction mechanism including neutral alcohol or alkoxide attack is under investigation.
50. Takita, R.; Fukuta, Y.; Tsuji, R.; Ohshima, T.; Shibasaki, M. Org. Lett. 2005, 7, 1363.
51. Ho, T.-L. Hard and Soft Acids and Bases Principle in Organic Chemistry; Academic Press: New York, 1977.