Chemoselective, Regioselective, and E/Z-Diastereoselective Synthesis of 2-Alkylidenetetrahydrofurans by Sequential Reactions of Ambident Dianions and Monoanions

Journal of Organic Chemistry

Volumn 68, Issue 25, 2003, Pages 9742-9746

  Langer, Peter ^a   Bellur, Esen ^a  

^a UNIVERSITY OF GREIFSWALD   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

REGIOSELECTIVITY;

ALKYLATION; DERIVATIVES; NEGATIVE IONS;

ESTERS;

1 BROMO 2 CHLOROETHANE; 1,3 DICARBONYL DERIVATIVE; ANION; BETA OXOCARBOXYLIC ACID ESTER; CARBANION; CARBON; CARBONYL DERIVATIVE; CHLOROETHANE; DIANION; ESTER DERIVATIVE; HALIDE; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CRYSTAL STRUCTURE; CYCLIZATION; DIASTEREOISOMER; ISOMERISM; METHODOLOGY; NUCLEAR OVERHAUSER EFFECT; PROTON TRANSPORT; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; THERMODYNAMICS;

EID: 0344666661     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034966f     Document Type: Article

References (50)

1. (a) For review, see: Boivin, T. L. B. Tetrahedron 1987, 43, 3309 and references therein.
2. (b) Barrett, A. G, M.; Sheth, H. G. J. Org. Chem. 1983, 48, 5017.
3. (c) Rao, Y. S. Chem. Rev. 1976, 76, 625.
4. (d) Pattenden, G. Prog. Chem. Nat. Prod. 1978, 35, 133.
5. (e) Knight, D. W. Contemp. Org. Synth. 1994, 1, 287.
6. (f) Gerlach, H,; Wetter, H. Helv. Chim. Acta 1974, 57, 2306,
7. (g) Schmidt, U.; Gombos, J,; Haslinger, E.; Zak, H. Chem, Ber. 1976, 109, 2628.
8. (h) Bartlett, P. A.; Meadows, J. D.; Ottow, E. J. Am. Chem. Soc. 1984, 106, 5304.
9. (i) Bryson, T. A. J. Org. Chem. 1973, 38, 3428.
10. (j) Yamaguchi, M.; Hirao, I. Chem. Lett. 1985, 337.
11. For the synthesis of nonactates from 2-alkylidenetetrahydrofurans, see: Lygo, B.; O'Connor, N.; Wilson, P. R. Tetrahedron 1988, 22, 6881.
12. For information about tetronasin, see: Boons, G.-J.; Clase, J. A.; Lennon, I. C.; Ley, S. V.; Staunton, J. Tetrahedron 1995, 51, 5417 and references therein.
13. For information about tetronomycin, see: Iqbal, J.; Pandey, A.; Chauhan, B. P. S. Tetrahedron 1991, 47, 4143.
14. Booth, P. M.; Fox, C. M. J.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1987, 121.
15. (a) Marvell, E. N.; Titterington, D. Tetrahedron Lett. 1980, 2123.
16. (b) Tsuji, J.; Kobayashi, Y.; Kataoka, H,; Takahashi, T. Tetrahedron Lett. 1980, 1475.
17. Wang, T.; Chen, J.; Landrey, D. W.; Zhao, K. Synlett 1995, 543.
18. For carbohydrate derived bicyclic 2-alkylidenetetrahydrofurans, see: (a) Al-Tel, T. H.; Voelter, W. J. Chem. Soc., Chem. Commun. 1995, 239.
19. (b) Al-Tel, T. H.; Meisenbach, M.; Voelter, W. Liebigs Ann. 1995, 689.
20. Arai, H.; Miyajima, H.; Mushiroda, T.; Yamamoto, Y. Chem. Pharm. Bull. 1989, 12, 3229.
21. Mori, K.; Sasaki, M.; Tamada, S.; Suguro, T,; Masuda, S. Tetrahedron 1979, 35, 1601.
22. For reviews of cyclization reactions of free and masked 1,3-dicarbonyl dianions, see: (a) Langer, P, Chem.-Eur. J. 2001, 7, 3858.
23. (b) Langer, P. Synthesis 2002, 441.
24. (a) Weiler, L. J. Am. Chem. Soc. 1970, 92, 6702.
25. (b) Seebach, D.; Ehrig, V. Angew. Chem. 1974, 86, 446; Angew. Chem., Int. Ed. Engl. 1974, 13, 401.
26. (b) Seebach, D.; Ehrig, V. Angew. Chem. 1974, 86, 446; Angew. Chem., Int. Ed. Engl. 1974, 13, 401.
27. (a) Langer, P.; Holtz, E.; Karimé, I.; Saleh, N. N. R. J. Org. Chem. 2001, 66, 6057.
28. (b) See also: Lambert, P. H.; Vaultier, M.; Carrié, R. J. Org. Chem. 1985, 50, 5352.
29. For cyclization reactions of dianions with difunctional alkyl halides, see: (a) Bahl, J. J.; Bates, R. B.; Beavers, W. A.; Mills, N. S. J. Org. Chem. 1976, 41, 1620.
30. (b) Hirai, K.; Iwano, Y. Tetrahedron Lett. 1979, 2031.
31. (c) Bilyard, K. G.; Garratt, P. J.; Hunter, R.; Lete, E. J. Org. Chem. 1982, 47, 4731.
32. Recently, the two-step synthesis of annelated imidazoles by cyclization of dilithiated 2-methylbenzimidazole with 1-bromo-2-chloroethane has been reported. McClure, J. R.; Custer, J. H.; Schwarz, H. D.; Lill, D. A. Synlett 2000, 710.
33. The cyclization of 1-bromo-2-chloroethane with the dianion of 2-methylindole, generated by the use of Lochmann-Schlosser base: Katritzky, A. R.; Fali, C. N.; Li, J. J. Org. Chem. 1997, 62, 4148.
34. Brandänge, S.; Lindqvist, B. Acta Chem. Scand. 1989, 43, 807.
35. Hampton, K. G.; Light, R. J.; Hauser, C. R. J. Org. Chem. 1965, 30, 1413.
36. Barry, C. E., III; Bates, R. B.; Beavers, W. A.; Camou, F. A.; Gordon, B., III; Hsu, H. F.-J.; Mills, N. S.; Ogle, C. A.; Siahaan, T. J.; Suvannachut, K.; Taylor, S. R.; White, J. J.; Yager, K. M. Synlett 1991, 207.
37. Hampton, K. G.; Christie, J. J. J. Org. Chem. 1976, 41, 2772.
38. Sum, P.-E.; Weiler, L. Can. J. Chem. 1977, 55, 996.
39. For stereoelectronic considerations related to the regioselectivity of cyclizations, see: Baldwin, J. E.; Kruse, L. I. J. Chem. Soc., Chem. Commun. 1977, 233.
40. For the configuration of 1,3-dicarbonyl enolates, see: (a) Rhoads, S. J. ; Holder, R. W. Tetrahedron 1969, 25, 5443.
41. (b) Miller, B.; Margulies, H.; Drabb, T., Jr.; Wayne, R. Tetrahedron Lett. 1970, 3801.
42. (c) Miller, B.; Margulies, H.; Drabb, T., Jr.; Wayne, R. Tetrahedron Lett. 1970, 3805.
43. (d) Entenmann, G. Tetrahedron Lett. 1975, 4241.
44. (e) Cambillau, C.; Sarthou, P.; Bram, G. Tetrahedron Lett. 1976, 281.
45. For a review of the structure of lithium enolates, see: (f) Seebach, D. Angew. Chem. 1988, 100, 1685; Angew. Chem., Int. Ed. Engl. 1988, 27, 1624.
46. For a review of the structure of lithium enolates, see: (f) Seebach, D. Angew. Chem. 1988, 100, 1685; Angew. Chem., Int. Ed. Engl. 1988, 27, 1624.
47. (a) Langer, P.; Freifeld, I. Chem.-Eur. J. 2001, 7, 565.
48. (b) Langer, P.; Armbrust, H.; Eckardt, T. Chem.-Eur. J. 2002, 8, 1443.
49. (c) Langer, P.; Holtz, E.; Saleh, N. N. R. Chem.-Eur. J. 2002, 8, 917.
50. These crystal structure analyses include compound 5h in ref 13a and recently prepared 4-methoxy-2-alkylidenetetrahydrofurans.