One-pot transformation of silyl enol ethers into 1,3-dienes: In situ generation of alkenyl nonaflates and subsequent Heck reactions - Scope and limitations

European Journal of Organic Chemistry

Volumn , Issue 21, 2002, Pages 3646-3658

  Lyapkalo, Ilya M ^a   Webel, Matthias ^b   Reißig, Hans Ulrich ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

^b DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

Alkenyl nonaflates; Dienes; Fluorides; Palladium catalysis; Silyl enol ethers

Indexed keywords

ACRYLIC ACID BUTYL ESTER; ACRYLIC ACID METHYL ESTER; ALKADIENE; ALKENE; ALKENYL GROUP; ETHER DERIVATIVE; FLUORIDE; PALLADIUM; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0036845358     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200211)2002:21<3646::AID-EJOC3646>3.0.CO;2-D     Document Type: Article

References (62)

1. [1a] Organikum, 21. Ed.; Wiley-VCH: Weinheim 2001, pp. 408-411.
2. [1b] H. Beyer. W. Walter; Lehrbuch der Organischen Chemie; 23. Ed.; (Eds.: W. Walter, W. Franke); Hirzel: Stuttgart, Leipzig 1998, pp. 408-409.
3. [1c] A. Streitwieser, C. H. Heathcock, E. M. Kosower; Organische Chemie; 2. Ed.; Wiley-VCH: Weinheim 2001, p. 1028.
4. [1b] F A. Carey, R. J. Sundberg, Organische Chemie; (Eds.: H.-J. Schäfer, D. Hoppe, G. Erker); Wiley-VCH: Weinheim 1995, pp. 1161-1162.
5. [2a] R. F. Heck, Org. React. (N. Y.) 1982, 27, 345-390.
6. [2b] R. F. Heck, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming); Pergamon Press: Oxford, 1991; Vol. 4.
7. [2c] L. E. Overman, Pure Appl. Chem. 1994, 66, 1423-1430.
8. [2d] A. de Meijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473-2506; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379-2411.
9. [2d] A. de Meijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473-2506; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379-2411.
10. [2e] T. Jeffery, In Advances in Metal-Organic Chemistry; L. S. Liebeskind, Ed.; Jai Press Inc: Greenwich, CT, 1996, Vol. 5.
11. [2f] J. T. Link, L. E. Overman, Chemtech 1998, 28, 19-26.
12. [2g] G. T. Crisp, Chem. Soc. Rev. 1998, 27, 427-436.
13. [2h] J. T. Link, L. E. Overman, in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH: New York, 1998.
14. [2i] I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009-3066 and references cited therein.
15. [3a] W. J. Scott, J. E. McMurry, Acc. Chem. Res. 1988,21, 47-54.
16. [3b] K. Ritter, Synthesis 1993, 735-762.
17. [4a] S. Bräse, A. de Meijere, Angew. Chem. 1995, 107, 2741-2743; Angew. Chem. Int. Ed. Engl. 1995, 34, 2545-2547.
18. [4a] S. Bräse, A. de Meijere, Angew. Chem. 1995, 107, 2741-2743; Angew. Chem. Int. Ed. Engl. 1995, 34, 2545-2547.
19. [4b] K. Voigt, P. von Zezschwitz, K. Rosauer, A. Lansky, A. Adams, O. Reiser, A. de Meijere, Eur. J. Org. Chem. 1998, 1521-1534.
20. [4c] S. Bräse, Synlett 1999, 1654-1656.
21. [4d] A. Wada, Y. Ieki, M. Ito, Synlett 2002, 1061-1063.
22. [4e] For the use of aryl nonaflates, see [4e] M. Rottlaender, P. Knochel, J. Org. Chem. 1998, 63, 203-208.
23. I. M. Lyapkalo, M. Webel, H.-U. Reißig, Eur. J. Org. Chem. 2002, 1015-1025.
24. M. Webel, H.-U. Reißig, Synlett 1997, 1141-1142.
25. M. Webel, Dissertation, Technische Universität Dresden, 2000.
26. I. M. Lyapkalo, M. Webel, H.-U. Reißig, Eur. J. Org. Chem. 2001, 4189-4194.
27. I. M. Lyapkalo, M. Webel, H.-U. Reissig, Synlett 2001, 1293-1295.
28. I. M. Lyapkalo, H.-U. Reißig, unpublished results.
29. A. Burini, S. Cacchi, P. Pace, B. R. Pietroni, Synlett 1995, 677-679.
30. 2Me groups in 10b was rigorously established by the selective proton decoupling method.
31. Any possible epimerisations and/or cycloreversions of 10b while boiling in PhC1 were ruled out by a control experiment conducted in the absence of DDQ under otherwise identical conditions, thereafter indicating no changes of a sample of 10b.
32. For comparison, a [4 + 2] cycloaddition between methyl acrylate and -penta-2,4-dienoic acid required heating at 110 °C to proceed, giving all four possible isomers, see: L. E. Overman, G. F. Taylor, K. N. Houk, L. N. Domelsmith, J. Am. Chem. Soc. 1978, 100, 3182-3189.
33. We also observed this compound in the one-pot reaction, but could not separate it from the main coupling product 9.
34. P. J. Stang, M. Hanack, L. R. Subramanian, Synthesis 1982, 85-126.
35. Alternatively, an E,Z isomerisation of the C,C double bond favouring the thermodynamically more stable E isomer may be operative under the reaction conditions, see: W. J. Scott, M. R. Peña, K. Swärd, S. J. Stoessel, J. K. Stille, J. Org. Chem. 1985, 50, 2302-2308; cf. ref.[2a].
36. W. Yu, Z. Jin, Tetrahedron Lett. 2001, 42, 369-372.
37. The detected NMR signals matched those described in the literature: M. Hesse, H. Meier, B. Zeeh; Spectroscopic Methods in Organic Chemistry; Thieme, Stuttgart, 1997, p. 186.
38. 2NEt in hexane at room temp. for 26 h.
39. This method was efficiently used for a highly selective preparation of -1d: S. Matsuzawa, Y. Horiguchi, E. Nakamura, I. Kuwajima, Tetrahedron 1989, 45, 349-362.
40. M. E. Jung, C. A. McCombs, Y. Takeda, Y.-G. Pan, J. Am. Chem. Soc. 1981, 103, 6677-6685.
41. M. Asaoka, H. Takei, Tetrahedron Lett. 1987, 28, 6343-6346.
42. J. Levisalles, D. Villemin, Tetrahedron 1980, 36, 3181-3186.
43. C. Thom, P. Kocienski, Synthesis 1992, 582-586.
44. B. M. Trost, L. Weber, P. Strege, T. J. Fullerton, T. J. Dietsche, J Am. Chem. Soc. 1978, 100, 3426-3435.
45. K. M. Bushan, G. V. Rao, T. Soujanya, V. J. Rao, S. Saha, A. Samanta, J. Org. Chem. 2001, 66, 681-688.
46. T. A. Shustrova, N. N. Belyaev, M. D. Stadnichuk, J. Gen. Chem. USSR, Engl. Transl. 1984, 54, 2492-2493; Zh. Obshch. Khim. 1984, 54, 2781-2783.
47. T. A. Shustrova, N. N. Belyaev, M. D. Stadnichuk, J. Gen. Chem. USSR, Engl. Transl. 1984, 54, 2492-2493; Zh. Obshch. Khim. 1984, 54, 2781-2783.
48. N. Krause, J. Org. Chem. 1992, 57, 3509-3512.
49. [30a] P. Seneci, M. Caspani, F. Monti, L. Carrano, S. Lociuro, R. Ciabatti, Synth. Commun. 1997, 27, 795-810.
50. 1H NMR of the closely related diethyl ester: J. Voss, W. Schmueser, K. Schlapkohl, J. Chem. Res. S (Synopses) 1977, 6, 144-145;
51. see also ref[13].
52. B. W. Larner, A. T. Peters, J. Chem. Soc. 1952, 680-686.
53. [32a] C. R. Unelius, A. Eiras, P. Witzgall, M. Bengtsson, A. Kovaleski, E. F. Vilela, A.-K. Borg-Karlson, Tetrahedron Lett. 1996, 37, 1505-1508.
54. [32b] C. R. Unelius, I. Liblikast, R. Mozuraitis, Acta Chem. Scand. 1998, 52, 930-934.
55. E D. Lewis, D. K. Howard, S. V. Barancyk, J. D. Oxman, J. Am. Chem. Soc. 1986, 108, 3016-3023.
56. R. Tamura, M. Kato, K. Saegusa, M. Kakihana, D. Oda, J. Org. Chem. 1987, 52, 4121-4124.
57. [35a] G. Saucy, R. Marbet, H. Lindlar, O. Isler, Helv. Chim. Acta 1959, 42, 1945-1955.
58. [35b] R. C. Cookson, M. C. Cramp, P. J. Parsons, J. Chem. Soc., Chem. Commun. 1980, 197-198.
59. For NMR of the closely related Et ester, see: H. Marschall, J. Penninger, P. Weyerstahl, Liebigs Ann. Chem. 1982, 49-67.
60. T. A. Engler, W. Falter, Synth. Commun. 1988, 18, 783-790.
61. K. Takaki, Y. Itono, A. Nagafuji, Y. Naito, T. Shishido, K. Takehira, Y. Makioka, Y. Taniguchi, Y. Fujiwara, J. Org. Chem. 2000, 65, 475-481.
62. G. Büchi, H. Wüest, J. Org. Chem. 1979, 44, 546-549.