Catalyzed Reactions of Enol Ethers with SN1 Active Groups: A Novel Method for the Preparation of α-Alkylated Ketones

Advanced Synthesis and Catalysis

Volumn 345, Issue 8, 2003, Pages 1017-1030

  Gansäuer, Andreas ^a   Fielenbach, Doris ^a   Stock, Christoph ^a   Geich Gimbel, Daniel ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

Alkylation; Boron; Catalysis; Copper; Enolates; Ketones; Lewis acids

Indexed keywords

ALDEHYDE; DEUTERIUM; ETHER DERIVATIVE; KETONE DERIVATIVE; SOLVENT;

ALKYLATION; ALLYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CROSSOVER PROCEDURE; METHODOLOGY;

EID: 0242607625     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200303059     Document Type: Article

References (53)

1. For recent reviews see: a) D. Caine, in Comprehensive Organic Synthesis, (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, Vol. 3, p. 1-63; b) D. L. Hughes, in Comprehensive Asymmetric Catalysis, (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, Vol. 1, p. 1273.
2. For recent reviews see: a) D. Caine, in Comprehensive Organic Synthesis, (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, Vol. 3, p. 1-63; b) D. L. Hughes, in Comprehensive Asymmetric Catalysis, (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, Vol. 1, p. 1273.
3. For some recent references see: a) M. Palucki, S. L. Buchwald, J. Am. Chem. Soc. 1997, 119, 11108; b) B. M. Trost, G. M. Schroeder, J. Am. Chem. Soc. 1999, 121, 6759; c) M. Braun, F. Laicher, T. Meier, Angew. Chem. 2000, 112, 3637; Angew. Chem. Int. Ed. 2000, 39, 3494.
4. For some recent references see: a) M. Palucki, S. L. Buchwald, J. Am. Chem. Soc. 1997, 119, 11108; b) B. M. Trost, G. M. Schroeder, J. Am. Chem. Soc. 1999, 121, 6759; c) M. Braun, F. Laicher, T. Meier, Angew. Chem. 2000, 112, 3637; Angew. Chem. Int. Ed. 2000, 39, 3494.
5. For some recent references see: a) M. Palucki, S. L. Buchwald, J. Am. Chem. Soc. 1997, 119, 11108; b) B. M. Trost, G. M. Schroeder, J. Am. Chem. Soc. 1999, 121, 6759; c) M. Braun, F. Laicher, T. Meier, Angew. Chem. 2000, 112, 3637; Angew. Chem. Int. Ed. 2000, 39, 3494.
6. For some recent references see: a) M. Palucki, S. L. Buchwald, J. Am. Chem. Soc. 1997, 119, 11108; b) B. M. Trost, G. M. Schroeder, J. Am. Chem. Soc. 1999, 121, 6759; c) M. Braun, F. Laicher, T. Meier, Angew. Chem. 2000, 112, 3637; Angew. Chem. Int. Ed. 2000, 39, 3494.
7. a) B. M. Trost, Science 1991, 254, 1471;
8. b) B. M. Trost, Angew. Chem. 1995, 107, 285; Angew. Chem. Int. Ed. Engl. 1995, 34, 259.
9. b) B. M. Trost, Angew. Chem. 1995, 107, 285; Angew. Chem. Int. Ed. Engl. 1995, 34, 259.
10. M. T. Reetz, Angew. Chem. 1982, 94, 97; Angew. Chem. Int. Ed. Engl. 1982, 21, 96.
11. M. T. Reetz, Angew. Chem. 1982, 94, 97; Angew. Chem. Int. Ed. Engl. 1982, 21, 96.
12. a) G. W. Kabalka, C. Narayana, N. K. Reddy, Synth. Commun. 1992, 22, 1793;
13. b) J. F. W. McOmie, M. L. Watts, D. E. West, Tetrahedron 1968, 24, 2289;
14. c) M. H. Park, R. Takeda, K. Nakanishi, Tetrahedron Lett. 1987, 28, 3823.
15. a) H. Frauenrath, Synthesis 1989, 721;
16. b) R. J. Ferrier, S. Middleton, Chem. Rev. 1993, 93, 2779;
17. c) N. A. Petasis, S.-P. Lu, J. Am. Chem. Soc. 1995, 117, 6394;
18. d) A. B. Smith III, P. R. Verhoest, K. P. Minbiole, J. J. Lim, Org. Lett. 1999, 1, 909.
19. a) N. A. Petasis, in Transition Metals for Organic Synthesis, (Eds.: M. Beller, C. Bolm), Wiley-VCH: Weinheim, 1998, Vol. 1, p. 361;
20. b) S. Otsuka, K. Tani, in Transition Metals for Organic Synthesis, (Eds.: M. Beller, C. Bolm), Wiley-VCH: Weinheim, 1998, Vol. 1, p. 147;
21. c) Y. Okimoto, S. Sakaguchi, Y. Ishii, J. Am. Chem. Soc. 2002, 124, 1590.
22. For a recent discussion of the stability of cations see: H. Mayr, B. Kempf, A. R. Ofial, Acc. Chem. Res. 2003, 36, 66 and references cited therein.
23. M. P. Sibi, G.R. Cook, in Lewis Acids in Organic Synthesis, (Ed.: H. Yamamoto), Wiley-VCH: Weinheim, 2001, Vol. 2, p. 543.
24. a) K. Ishihara, N. Hanaki, M. Funahashi, M. Miyata, H. Yamamoto, Bull. Chem. Soc. Jpn. 1995, 68, 1721;
25. b) D. J. Parks, W. E. Piers, J. Am. Chem. Soc. 1996, 118, 9440;
26. c) W. E. Piers, T. Chivers, T. Chem. Soc. Rev. 1997, 345;
27. d) K. Ishihara, H. Yamamoto, Eur. J. Org. Chem. 1999, 527.
28. a) J. J. Gajewski, Acc. Chem. Res. 1997, 30, 219;
29. b) H. Ito, T. Taguchi, Chem. Soc. Rev. 1999, 28, 43.
30. For work on catalytic [3,3]-rearrangements see: a) J. Borgulya, R. Madeja, P. Fahrni; H.-J. Hansen, H. Schmid, R. Barner, Helv. Chim. Acta 1973, 56, 14; b) K. Nonoshita, H. Banno, K. Maruoka, H. Yamamoto, J. Am. Chem. Soc. 1990, 112, 316; c) S. Saito, K. Shimada, H. Yamamoto, Synlett 1996, 720; d) B. M. Trost, G. M. Schroeder, J. Am. Chem. Soc. 2000, 122, 3785; e) M. Hiersemann, L. Abraham, Org. Lett. 2001, 3, 49; f) L. Abraham, R. Czerwonka, M. Hiersemann, Angew. Chem. 2001, 113, 4835; Angew. Chem. Int. Ed. 2001, 40, 4700.
31. For work on catalytic [3,3]-rearrangements see: a) J. Borgulya, R. Madeja, P. Fahrni; H.-J. Hansen, H. Schmid, R. Barner, Helv. Chim. Acta 1973, 56, 14; b) K. Nonoshita, H. Banno, K. Maruoka, H. Yamamoto, J. Am. Chem. Soc. 1990, 112, 316; c) S. Saito, K. Shimada, H. Yamamoto, Synlett 1996, 720; d) B. M. Trost, G. M. Schroeder, J. Am. Chem. Soc. 2000, 122, 3785; e) M. Hiersemann, L. Abraham, Org. Lett. 2001, 3, 49; f) L. Abraham, R. Czerwonka, M. Hiersemann, Angew. Chem. 2001, 113, 4835; Angew. Chem. Int. Ed. 2001, 40, 4700.
32. For work on catalytic [3,3]-rearrangements see: a) J. Borgulya, R. Madeja, P. Fahrni; H.-J. Hansen, H. Schmid, R. Barner, Helv. Chim. Acta 1973, 56, 14; b) K. Nonoshita, H. Banno, K. Maruoka, H. Yamamoto, J. Am. Chem. Soc. 1990, 112, 316; c) S. Saito, K. Shimada, H. Yamamoto, Synlett 1996, 720; d) B. M. Trost, G. M. Schroeder, J. Am. Chem. Soc. 2000, 122, 3785; e) M. Hiersemann, L. Abraham, Org. Lett. 2001, 3, 49; f) L. Abraham, R. Czerwonka, M. Hiersemann, Angew. Chem. 2001, 113, 4835; Angew. Chem. Int. Ed. 2001, 40, 4700.
33. For work on catalytic [3,3]-rearrangements see: a) J. Borgulya, R. Madeja, P. Fahrni; H.-J. Hansen, H. Schmid, R. Barner, Helv. Chim. Acta 1973, 56, 14; b) K. Nonoshita, H. Banno, K. Maruoka, H. Yamamoto, J. Am. Chem. Soc. 1990, 112, 316; c) S. Saito, K. Shimada, H. Yamamoto, Synlett 1996, 720; d) B. M. Trost, G. M. Schroeder, J. Am. Chem. Soc. 2000, 122, 3785; e) M. Hiersemann, L. Abraham, Org. Lett. 2001, 3, 49; f) L. Abraham, R. Czerwonka, M. Hiersemann, Angew. Chem. 2001, 113, 4835; Angew. Chem. Int. Ed. 2001, 40, 4700.
34. For work on catalytic [3,3]-rearrangements see: a) J. Borgulya, R. Madeja, P. Fahrni; H.-J. Hansen, H. Schmid, R. Barner, Helv. Chim. Acta 1973, 56, 14; b) K. Nonoshita, H. Banno, K. Maruoka, H. Yamamoto, J. Am. Chem. Soc. 1990, 112, 316; c) S. Saito, K. Shimada, H. Yamamoto, Synlett 1996, 720; d) B. M. Trost, G. M. Schroeder, J. Am. Chem. Soc. 2000, 122, 3785; e) M. Hiersemann, L. Abraham, Org. Lett. 2001, 3, 49; f) L. Abraham, R. Czerwonka, M. Hiersemann, Angew. Chem. 2001, 113, 4835; Angew. Chem. Int. Ed. 2001, 40, 4700.
35. For work on catalytic [3,3]-rearrangements see: a) J. Borgulya, R. Madeja, P. Fahrni; H.-J. Hansen, H. Schmid, R. Barner, Helv. Chim. Acta 1973, 56, 14; b) K. Nonoshita, H. Banno, K. Maruoka, H. Yamamoto, J. Am. Chem. Soc. 1990, 112, 316; c) S. Saito, K. Shimada, H. Yamamoto, Synlett 1996, 720; d) B. M. Trost, G. M. Schroeder, J. Am. Chem. Soc. 2000, 122, 3785; e) M. Hiersemann, L. Abraham, Org. Lett. 2001, 3, 49; f) L. Abraham, R. Czerwonka, M. Hiersemann, Angew. Chem. 2001, 113, 4835; Angew. Chem. Int. Ed. 2001, 40, 4700.
36. For work on catalytic [3,3]-rearrangements see: a) J. Borgulya, R. Madeja, P. Fahrni; H.-J. Hansen, H. Schmid, R. Barner, Helv. Chim. Acta 1973, 56, 14; b) K. Nonoshita, H. Banno, K. Maruoka, H. Yamamoto, J. Am. Chem. Soc. 1990, 112, 316; c) S. Saito, K. Shimada, H. Yamamoto, Synlett 1996, 720; d) B. M. Trost, G. M. Schroeder, J. Am. Chem. Soc. 2000, 122, 3785; e) M. Hiersemann, L. Abraham, Org. Lett. 2001, 3, 49; f) L. Abraham, R. Czerwonka, M. Hiersemann, Angew. Chem. 2001, 113, 4835; Angew. Chem. Int. Ed. 2001, 40, 4700.
37. For the deprotonation at the more hindered site of ketones in the presence of stoichiometric amount of a bulky aluminum Lewis acid see: S. Saito, M. Ito, H. Yamamoto, J. Am. Chem. Soc. 1997, 119, 611.
38. See, for example: R. T. Conlin, R. D. Miller, J. Michl, J. Am. Chem. Soc. 1979, 101, 7637 and references cited therein.
39. a) P. A. Grieco, J. D. Clark, C. T. Jagoe, J. Am. Chem. Soc. 1991, 113, 5488;
40. b) N. Palini, K. K. Balasubramanian, Tetrahedron Lett. 1993, 34, 5001;
41. M. T. Reetz, A. Gansäuer, Tetrahedron 1993, 49, 6025.
42. For a report on an explosion with 5 M LPDE see: R. A. Silva, Chem. Eng. News 1992, 70 (52), 2.
43. S. Winstein, E. Clippinger, A. H. Fainberg, R. Heck, G. C. Robinson, J. Am. Chem. Soc. 1956, 78, 328.
44. T. Okazoe, K. Takai, K. Oshima, K. Utimoto, J. Org. Chem. 1987, 52, 4410.
45. W. G. Dauben, T. J. Dietsche, J. Org. Chem. 1972, 37, 1212.
46. P. G. McDougal, J. G. Rico, Tetrahedron Lett. 1984, 25, 5977.
47. Y. Kawai, M. Hayashi, Y. Inaba, K. A. Saitou, A. Ohno, Tetrahedron Lett. 1998, 39, 5225.
48. G. L. Borosky, A. B. Adriana, R. A. Rossi, J. Org. Chem. 1990, 55, 3705.
49. S. H. Pines, A. W. Douglas, J. Org. Chem. 1977, 42, 2786.
50. A. V. Malkov, I. R. Baxendale, D. Dvorak, D. J. Mansfield, P. Kokovsky, J. Org. Chem. 1999, 64, 2737.
51. S. P. Kolis, M. E. Kopach, R. Liu, W. D. Harman, J. Org. Chem. 1997, 62, 130.
52. L. Duhamel, J.-M. Poirier, J. Org. Chem. 1979, 44, 3585.
53. J. Boivin, E. Fouquet, S. Z. Zard, Tetrahedron Lett. 1990, 31, 85.