Bidirectional and convergent routes to oligo(tetrahydrofurans)

Chemistry - A European Journal

Volumn 3, Issue 7, 1997, Pages 1170-1180

  Koert, Ulrich ^a   Stein, Matthias ^a   Wagner, Holger ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

Oligomers; Polyethers; Tetrahydrofurans; Williamson reaction

Indexed keywords

EID: 0030752370     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.19970030723     Document Type: Article

References (52)

1. U. Koert, Synthesis 1995, 115.
2. a) M. C. Zafra-Polo, M. C. Gonzalez, E. Estornell, S. Sahpaz, D. Cortes, Phytochemistry 1996, 42, 253;
3. b) B. Figadere, Acc. Chem. Res. 1995, 28, 359;
4. c) R. Hoppe, H.-D. Scharf, Synthesis 1995, 1447.
5. Z.-M. Gu, X.-P. Fang, L. Zeng, J. L. McLaughlin, Tetrahedron Lett. 1994, 35, 5367.
6. a) U. Koert, M. Stein, K. Harms, Angew. Chem. 1994, 106, 1238; Angew. Chem. Int. Ed. Engl. 1994, 33, 1180;
7. a) U. Koert, M. Stein, K. Harms, Angew. Chem. 1994, 106, 1238; Angew. Chem. Int. Ed. Engl. 1994, 33, 1180;
8. b) H. Wagner, K. Harms, U. Koert, S. Meder, G. Boheim, Angew. Chem. 1996, 108, 2836; Angew. Chem. Int. Ed. Engl. 1996, 35, 2643; for podand-like cation complexation of oligo-THFs see ref. [2c] and c) S. Sasaki, H. Naito, K. Maruta, E. Kawahara, M. Maeda, Tetrahedron Lett. 1994, 35, 3337.
9. b) H. Wagner, K. Harms, U. Koert, S. Meder, G. Boheim, Angew. Chem. 1996, 108, 2836; Angew. Chem. Int. Ed. Engl. 1996, 35, 2643; for podand-like cation complexation of oligo-THFs see ref. [2c] and c) S. Sasaki, H. Naito, K. Maruta, E. Kawahara, M. Maeda, Tetrahedron Lett. 1994, 35, 3337.
10. b) H. Wagner, K. Harms, U. Koert, S. Meder, G. Boheim, Angew. Chem. 1996, 108, 2836; Angew. Chem. Int. Ed. Engl. 1996, 35, 2643; for podand-like cation complexation of oligo-THFs see ref. [2c] and c) S. Sasaki, H. Naito, K. Maruta, E. Kawahara, M. Maeda, Tetrahedron Lett. 1994, 35, 3337.
11. Representative approaches to bi-THFs; a) S. C. Sinha, A. Sinha-Bagchi, A. Yazbak, E. Keinan, Tetrahedron Lett. 1995, 36, 9257; b) S. C. Sinha, A. Sinha, A. Yazbak, E. Keinan, J. Org. Chem. 1996, 61, 7640; c) Z. Ruan, P. Wilson, D. R. Mootoo, Tetrahedron Lett. 1996, 37, 3619; d) T. R. Hoye, L. Tan, ibid. 1995, 36, 1981; e) H. Naito, E. Kawahara, K. Maruta, M. Maeda, S. Sasaki, J. Org. Chem. 1995, 60, 4419; f) B. Figadere, C. Chaboche, C. Peyrat, A. Andre, Tetrahedron Lett. 1993, 34, 8093; g) J. Wöhrle, A. Clen, M. Peterek, H. D. Scharf, ibid. 1996, 37, 7001; h) U. Koert, ibid. 1994, 35, 2517; h) Z. J. Yao, Y-L. Wu, J. Org. Chem. 1995, 60, 1170; see also: h) B. M. Trost, T. L. Calkins, Tetrahedron Lett. 1995, 36, 6021.
12. Representative approaches to bi-THFs; a) S. C. Sinha, A. Sinha-Bagchi, A. Yazbak, E. Keinan, Tetrahedron Lett. 1995, 36, 9257; b) S. C. Sinha, A. Sinha, A. Yazbak, E. Keinan, J. Org. Chem. 1996, 61, 7640; c) Z. Ruan, P. Wilson, D. R. Mootoo, Tetrahedron Lett. 1996, 37, 3619; d) T. R. Hoye, L. Tan, ibid. 1995, 36, 1981; e) H. Naito, E. Kawahara, K. Maruta, M. Maeda, S. Sasaki, J. Org. Chem. 1995, 60, 4419; f) B. Figadere, C. Chaboche, C. Peyrat, A. Andre, Tetrahedron Lett. 1993, 34, 8093; g) J. Wöhrle, A. Clen, M. Peterek, H. D. Scharf, ibid. 1996, 37, 7001; h) U. Koert, ibid. 1994, 35, 2517; h) Z. J. Yao, Y-L. Wu, J. Org. Chem. 1995, 60, 1170; see also: h) B. M. Trost, T. L. Calkins, Tetrahedron Lett. 1995, 36, 6021.
13. Representative approaches to bi-THFs; a) S. C. Sinha, A. Sinha-Bagchi, A. Yazbak, E. Keinan, Tetrahedron Lett. 1995, 36, 9257; b) S. C. Sinha, A. Sinha, A. Yazbak, E. Keinan, J. Org. Chem. 1996, 61, 7640; c) Z. Ruan, P. Wilson, D. R. Mootoo, Tetrahedron Lett. 1996, 37, 3619; d) T. R. Hoye, L. Tan, ibid. 1995, 36, 1981; e) H. Naito, E. Kawahara, K. Maruta, M. Maeda, S. Sasaki, J. Org. Chem. 1995, 60, 4419; f) B. Figadere, C. Chaboche, C. Peyrat, A. Andre, Tetrahedron Lett. 1993, 34, 8093; g) J. Wöhrle, A. Clen, M. Peterek, H. D. Scharf, ibid. 1996, 37, 7001; h) U. Koert, ibid. 1994, 35, 2517; h) Z. J. Yao, Y-L. Wu, J. Org. Chem. 1995, 60, 1170; see also: h) B. M. Trost, T. L. Calkins, Tetrahedron Lett. 1995, 36, 6021.
14. Representative approaches to bi-THFs; a) S. C. Sinha, A. Sinha-Bagchi, A. Yazbak, E. Keinan, Tetrahedron Lett. 1995, 36, 9257; b) S. C. Sinha, A. Sinha, A. Yazbak, E. Keinan, J. Org. Chem. 1996, 61, 7640; c) Z. Ruan, P. Wilson, D. R. Mootoo, Tetrahedron Lett. 1996, 37, 3619; d) T. R. Hoye, L. Tan, ibid. 1995, 36, 1981; e) H. Naito, E. Kawahara, K. Maruta, M. Maeda, S. Sasaki, J. Org. Chem. 1995, 60, 4419; f) B. Figadere, C. Chaboche, C. Peyrat, A. Andre, Tetrahedron Lett. 1993, 34, 8093; g) J. Wöhrle, A. Clen, M. Peterek, H. D. Scharf, ibid. 1996, 37, 7001; h) U. Koert, ibid. 1994, 35, 2517; h) Z. J. Yao, Y-L. Wu, J. Org. Chem. 1995, 60, 1170; see also: h) B. M. Trost, T. L. Calkins, Tetrahedron Lett. 1995, 36, 6021.
15. Representative approaches to bi-THFs; a) S. C. Sinha, A. Sinha-Bagchi, A. Yazbak, E. Keinan, Tetrahedron Lett. 1995, 36, 9257; b) S. C. Sinha, A. Sinha, A. Yazbak, E. Keinan, J. Org. Chem. 1996, 61, 7640; c) Z. Ruan, P. Wilson, D. R. Mootoo, Tetrahedron Lett. 1996, 37, 3619; d) T. R. Hoye, L. Tan, ibid. 1995, 36, 1981; e) H. Naito, E. Kawahara, K. Maruta, M. Maeda, S. Sasaki, J. Org. Chem. 1995, 60, 4419; f) B. Figadere, C. Chaboche, C. Peyrat, A. Andre, Tetrahedron Lett. 1993, 34, 8093; g) J. Wöhrle, A. Clen, M. Peterek, H. D. Scharf, ibid. 1996, 37, 7001; h) U. Koert, ibid. 1994, 35, 2517; h) Z. J. Yao, Y-L. Wu, J. Org. Chem. 1995, 60, 1170; see also: h) B. M. Trost, T. L. Calkins, Tetrahedron Lett. 1995, 36, 6021.
16. Representative approaches to bi-THFs; a) S. C. Sinha, A. Sinha-Bagchi, A. Yazbak, E. Keinan, Tetrahedron Lett. 1995, 36, 9257; b) S. C. Sinha, A. Sinha, A. Yazbak, E. Keinan, J. Org. Chem. 1996, 61, 7640; c) Z. Ruan, P. Wilson, D. R. Mootoo, Tetrahedron Lett. 1996, 37, 3619; d) T. R. Hoye, L. Tan, ibid. 1995, 36, 1981; e) H. Naito, E. Kawahara, K. Maruta, M. Maeda, S. Sasaki, J. Org. Chem. 1995, 60, 4419; f) B. Figadere, C. Chaboche, C. Peyrat, A. Andre, Tetrahedron Lett. 1993, 34, 8093; g) J. Wöhrle, A. Clen, M. Peterek, H. D. Scharf, ibid. 1996, 37, 7001; h) U. Koert, ibid. 1994, 35, 2517; h) Z. J. Yao, Y-L. Wu, J. Org. Chem. 1995, 60, 1170; see also: h) B. M. Trost, T. L. Calkins, Tetrahedron Lett. 1995, 36, 6021.
17. Representative approaches to bi-THFs; a) S. C. Sinha, A. Sinha-Bagchi, A. Yazbak, E. Keinan, Tetrahedron Lett. 1995, 36, 9257; b) S. C. Sinha, A. Sinha, A. Yazbak, E. Keinan, J. Org. Chem. 1996, 61, 7640; c) Z. Ruan, P. Wilson, D. R. Mootoo, Tetrahedron Lett. 1996, 37, 3619; d) T. R. Hoye, L. Tan, ibid. 1995, 36, 1981; e) H. Naito, E. Kawahara, K. Maruta, M. Maeda, S. Sasaki, J. Org. Chem. 1995, 60, 4419; f) B. Figadere, C. Chaboche, C. Peyrat, A. Andre, Tetrahedron Lett. 1993, 34, 8093; g) J. Wöhrle, A. Clen, M. Peterek, H. D. Scharf, ibid. 1996, 37, 7001; h) U. Koert, ibid. 1994, 35, 2517; h) Z. J. Yao, Y-L. Wu, J. Org. Chem. 1995, 60, 1170; see also: h) B. M. Trost, T. L. Calkins, Tetrahedron Lett. 1995, 36, 6021.
18. Representative approaches to bi-THFs; a) S. C. Sinha, A. Sinha-Bagchi, A. Yazbak, E. Keinan, Tetrahedron Lett. 1995, 36, 9257; b) S. C. Sinha, A. Sinha, A. Yazbak, E. Keinan, J. Org. Chem. 1996, 61, 7640; c) Z. Ruan, P. Wilson, D. R. Mootoo, Tetrahedron Lett. 1996, 37, 3619; d) T. R. Hoye, L. Tan, ibid. 1995, 36, 1981; e) H. Naito, E. Kawahara, K. Maruta, M. Maeda, S. Sasaki, J. Org. Chem. 1995, 60, 4419; f) B. Figadere, C. Chaboche, C. Peyrat, A. Andre, Tetrahedron Lett. 1993, 34, 8093; g) J. Wöhrle, A. Clen, M. Peterek, H. D. Scharf, ibid. 1996, 37, 7001; h) U. Koert, ibid. 1994, 35, 2517; h) Z. J. Yao, Y-L. Wu, J. Org. Chem. 1995, 60, 1170; see also: h) B. M. Trost, T. L. Calkins, Tetrahedron Lett. 1995, 36, 6021.
19. Representative approaches to bi-THFs; a) S. C. Sinha, A. Sinha-Bagchi, A. Yazbak, E. Keinan, Tetrahedron Lett. 1995, 36, 9257; b) S. C. Sinha, A. Sinha, A. Yazbak, E. Keinan, J. Org. Chem. 1996, 61, 7640; c) Z. Ruan, P. Wilson, D. R. Mootoo, Tetrahedron Lett. 1996, 37, 3619; d) T. R. Hoye, L. Tan, ibid. 1995, 36, 1981; e) H. Naito, E. Kawahara, K. Maruta, M. Maeda, S. Sasaki, J. Org. Chem. 1995, 60, 4419; f) B. Figadere, C. Chaboche, C. Peyrat, A. Andre, Tetrahedron Lett. 1993, 34, 8093; g) J. Wöhrle, A. Clen, M. Peterek, H. D. Scharf, ibid. 1996, 37, 7001; h) U. Koert, ibid. 1994, 35, 2517; h) Z. J. Yao, Y-L. Wu, J. Org. Chem. 1995, 60, 1170; see also: h) B. M. Trost, T. L. Calkins, Tetrahedron Lett. 1995, 36, 6021.
20. Representative approaches to bi-THFs; a) S. C. Sinha, A. Sinha-Bagchi, A. Yazbak, E. Keinan, Tetrahedron Lett. 1995, 36, 9257; b) S. C. Sinha, A. Sinha, A. Yazbak, E. Keinan, J. Org. Chem. 1996, 61, 7640; c) Z. Ruan, P. Wilson, D. R. Mootoo, Tetrahedron Lett. 1996, 37, 3619; d) T. R. Hoye, L. Tan, ibid. 1995, 36, 1981; e) H. Naito, E. Kawahara, K. Maruta, M. Maeda, S. Sasaki, J. Org. Chem. 1995, 60, 4419; f) B. Figadere, C. Chaboche, C. Peyrat, A. Andre, Tetrahedron Lett. 1993, 34, 8093; g) J. Wöhrle, A. Clen, M. Peterek, H. D. Scharf, ibid. 1996, 37, 7001; h) U. Koert, ibid. 1994, 35, 2517; h) Z. J. Yao, Y-L. Wu, J. Org. Chem. 1995, 60, 1170; see also: h) B. M. Trost, T. L. Calkins, Tetrahedron Lett. 1995, 36, 6021.
21. L. F. Tietze, Chem. Rev. 1996, 96, 115.
22. a) T. R. Hoye, J. C. Suhadolnik, Tetrahedron 1986, 42, 2855;
23. b) U. Koert, H. Wagner, M. Stein, Tetrahedron Lett. 1994, 35, 7629;
24. for related work in polyether synthesis, see c) S. L. Schreiber, T. Sammakia, B. Hulin, G. Schulte, J. Am. Chem. Soc. 1986, 108, 2106;
25. d) W. C. Still, A. G. Romero, ibid. 1986, 108, 2105;
26. e) I. Paterson, R. D.Tillyer, J. B. Smaill, Tetrahedron Lett. 1993, 34, 7137;
27. f) D. F. Taber, R. S. Bhamidipati, M. L. Thomas, J. Org. Chem. 1994, 59, 3442.
28. T. J. Beauchamp, J. P. Powers, S. D. Rychnovsky, J. Am. Chem. Soc. 1995, 117, 12873.
29. a) R. S. Boyce, R. M. Kennedy, Tetrahedron Lett. 1994, 35, 5133;
30. b) F. E. McDonald, T. B. Towne, J. Am. Chem. Soc. 1994, 116, 7921;
31. c) S. C. Sinha, A. Sinha-Bagchi, E. Keinan, ibid. 1995, 117, 1447.
32. a) H. Wagner, U. Koert, Angew. Chem. 1994, 106, 1939; Angew. Chem. Int. Ed. Engl. 1994, 33, 1873;
33. a) H. Wagner, U. Koert, Angew. Chem. 1994, 106, 1939; Angew. Chem. Int. Ed. Engl. 1994, 33, 1873;
34. b) for the combination of allylic stannahe chemistry and a multiple Williamson reaction, see J. A. Marshall, K. W. Hinkle, J. Org. Chem. 1996, 61, 4247.
35. For short communications of part of this work see refs. [4a] and [10a].
36. a) B. Küchler, G. Voss, H. Gerlach, Liebigs Ann. Chem. 1991, 545;
37. b) U. Koert, H. Wagner, U. Pidun, Chem. Ber. 1994, 127, 1447.
38. W. Boland, V. Hansen, L. Jaenicke, Synthesis 1979, 114.
39. R. A. Johnson, K. B. Sharpless in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, Weinheim, 1993, p. 227.
40. Preparation of 22 from tartaric acid: D. Seebach, H.-D. Kalinowsky, B. Bastani, G. Crass, H. Daum, H. Dörr, N. P. DuPreez, V. Ehrig, W. Langer, C. Nüssler, H.-A. Oei, M. Schmidt, Helv. Chim. Acta 1977, 60, 301; by asymmetric dihydroxylation from (E)-1,4-dichloro-2-butene: K. P. M. Vanhessche, Z.-M. Wang, K. B. Sharpless, Tetrahedron Lett. 1994, 35, 3469.
41. Preparation of 22 from tartaric acid: D. Seebach, H.-D. Kalinowsky, B. Bastani, G. Crass, H. Daum, H. Dörr, N. P. DuPreez, V. Ehrig, W. Langer, C. Nüssler, H.-A. Oei, M. Schmidt, Helv. Chim. Acta 1977, 60, 301; by asymmetric dihydroxylation from (E)-1,4-dichloro-2-butene: K. P. M. Vanhessche, Z.-M. Wang, K. B. Sharpless, Tetrahedron Lett. 1994, 35, 3469.
42. M. F. Perutz, G. Fermie, B. Luisi, B. Shaanan, R. C. Liddington, Acc. Chem. Res. 1987, 20, 309;
43. b) G. K. Ackers, J. H. Hazzard, TIBS, 1993, 385.
44. T. L. Hill, Cooperativity Theory in Biochemistry, Springer, New York, 1985.
45. S. Wolfe, C-K. Kim, K. Yang, N. Weinberg, Z. Shi, J. Am. Chem. Soc. 1995, 117, 4240.
46. a) A. Pfeil, J.-M. Lehn, J. Chem. Soc. Chem. Commun. 1992, 838:
47. b) T. M. Garrett, U. Koert, J.-M. Lehn, J. Phys. Org. Chem. 1992, 5, 529.
48. J. Thomaides, P. Maslak, R. Breslow, J. Am. Chem. Soc. 1988, 110, 3970.
49. U. Koert, M. Stein, H. Wagner, Liebigs. Ann. 1995, 1415.
50. P. K. Jadhav, K. S. Bhat, P. T. Perumal, H. C. Brown, J. Org. Chem. 1986, 51, 432.
51. H. Kotsuki, K. Matsumoto, H. Nishizawa, Tetrahedron Lett. 1991, 32, 4155.
52. P. Brougham, M. S. Cooper, D. A. Cummerson, H. Heaney, M. Thompson, Synthesis 1987, 1015.