Regio- and stereoselective synthesis of 2-alkylidene-hydrofurans by domino-cyclodialkylations of 1,3-dicarbonyl-dianions with 1-bromo-2- chloroethane

Synlett

Volumn , Issue 5, 2000, Pages 743-745

  Langer, Peter ^a   Karimé, Inass ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Ambident dianions; Cyclization reactions; Domino reactions; Regioselectivity; Stereoselective syntheses

Indexed keywords

BROMINE DERIVATIVE; CARBONYL DERIVATIVE; FURAN DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CYCLIZATION; STEREOCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS;

EID: 0034083374     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (41)

1. Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131.
2. a) Langer, P.; Stoll, M. Angew. Chem. Int. Ed. Engl. 1999, 38, 1803;
3. b) Langer, P.; Schneider, T.; Stoll, M.; Göbel, C.; Herbst-Irmer, R. Chem. Eur. J. 2000, in press.
4. a) Langer, P.; Döring, M.; Görls, H.; Beckert, R. Liebigs Ann./ Receuil 1997, 2553;
5. b) Langer, P.; Döring, M. Synlett 1998, 396;
6. c) Langer, P.; Döring, M. Synlett 1998, 399;
7. d) Langer, P.; Wuckelt, J.; Döring, M.; Beckert, R. Eur. J. Org. Chem. 1998, 1467;
8. e) Wuckelt, J.; Döring, M.; Langer, P.; Beckert, R.; Görls, H. J. Org. Chem. 1999, 64, 365;
9. f) Langer, P.; Döring, M. Chem. Commun. 1999, 2439;
10. g) Langer, P.; Wuckelt, J.; Döring, M.; Görls, H. J. Org. Chem. 2000, in press;
11. h) Langer, P.; Freifeld, I.; Holtz, E. Synlett 2000, in press.
12. For reviews of dianions, see: a) Maercker, A. Methoden Org. Chem. (Houben-Weyl) 4. Aufl., Bd. EI9d 1993, 448;
13. b) Thompson, C. M.; Green, D. Tetrahedron 1991, 47, 4223.
14. a) Bilyard, K. G.; Garratt, P. J.; Hunter, R.; Lete, E. J. Org. Chem. 1982, 47, 4731;
15. b) Bates, R. B.; Gordon, B.; Highsmith, T. K.; White, J. J. J. Org. Chem. 1984, 49, 2981;
16. c)Tanaka, K.; Horiuchi, H.; Yoda, H. J. Org. Chem. 1989, 54, 63;
17. d) Maercker, A.; Groos, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 210.
18. a) Weiler, L. J. Am. Chem. Soc. 1970, 92, 6702;
19. b) Seebach, D.; Ehrig, V. Angew. Chem. Int. Ed. Engl. 1974, 13, 401.
20. For the use of 1,3-dicarbonyl dianions in natural product syntheses, see: a) Hoffmann, R. W.; Ladner, W.; Steinbach, K.; Massa, W.; Schmidt, R.; Snatzke, G. Chem. Ber. 1981, 114, 2786;
21. b) Williard, P. G.; Grab, L. A.; de Laszlo, S. E. J. Org. Chem. 1983, 48, 1123;
22. c) Clarke, T.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1987, 131;
23. d) Lygo, B. Tetrahedron 1988, 44, 6889;
24. e) Gilbreath, S. G.; Harris, C. M.; Harris, T. M. J. Am. Chem. Soc. 1988, 110, 6172.
25. Sum, P.-E.; Weiler, L. Can. J. Chem. 1977, 55, 996.
26. Hampton, K. G.; Light, R. J.; Hauser, C. R. J. Org. Chem. 1965, 30, 1413.
27. Barry III, C. E.; Bates, R. B.; Beavers, W. A.; Camou, F. A.; Gordon III, B.; Hsu, H. F.-J.; Mills, N. S.; Ogle, C. A.; Siahaan, T. J.; Suvannachut, K.; Taylor, S. R.; White, J. I.; Yager, K. M. Synlett 1991, 207.
28. Hampton, K. G.; Christie, J. J. J. Org. Chem. 1976, 41, 2772.
29. For the formation of open-chain products, see: Lambert, P. H.; Vaultier, M.; Carrié, R. J. Org. Chem. 1985, 50, 5352.
30. a) Barrett, A. G. M.; Sheth, H. G. J. Org. Chem. 1983, 48, 5017;
31. b) Rao, Y. S. Chem. Rev. 1976, 76, 625;
32. c) Pattenden, G. Prog. Chem. Nat. Prod. 1978, 55, 133;
33. d) Knight, D. W. Contemp. Org. Synth. 1994, 1, 287.
34. 3: C, 61.52; H, 7.74. Found: C, 61.74; H, 7.60. All products gave correct spectroscopic and analytical and/ or high resolution mass data.
35. For stereoelectronic considerations related to the regioselectivity of cyclizations, see: Baldwin, J. E.; Kruse, L. I. J. Chem. Soc., Chem. Commun. 1977, 233.
36. For the configuration of monoanions of 1,3-dicarbonyl compounds, see: a) Rhoads, S. J.; Holder, R. W. Tetrahedron 1969, 25, 5443;
37. b) Miller, B.; Margulies, H.; Drabb Jr., T.; Wayne, R. Tetrahedron Lett. 1970, 3801;
38. c) Miller, B.; Margulies, H.; Drabb Jr., T.; Wayne, R. Tetrahedron Lett. 1970, 3805; Entenmann, G. Tetrahedron Lett. 1975, 4241;
39. c) Miller, B.; Margulies, H.; Drabb Jr., T.; Wayne, R. Tetrahedron Lett. 1970, 3805; Entenmann, G. Tetrahedron Lett. 1975, 4241;
40. e) Cambillau, C.; Sarthou, P.; Bram, G. Tetrahedron Lett. 1976, 281.
41. Vinick, F. J.; Pan, Y.; Gschwend, H. W. Tetrahedron Lett. 1978, 44, 4221.