Chelated enolates of amino acid esters - New and efficient nucleophiles for isomerization-free, stereoselective palladium-catalyzed allylic substitutions

European Journal of Organic Chemistry

Volumn , Issue 21, 2001, Pages 4067-4076

  Kazmaier, Uli ^a,b   Zumpe, Franz L ^a,b  

^a UNIVERSITY OF HEIDELBERG   (Germany)

^b SAARLAND UNIVERSITY   (Germany)

Author keywords

Allylic alkylation; Amino acids; Enolates; Isomerization; Palladium

Indexed keywords

ALKENE DERIVATIVE; ALLYL COMPOUND; AMINO ACID DERIVATIVE; CARBONIC ACID DERIVATIVE; ESTER DERIVATIVE; PALLADIUM;

ALKYLATION; ARTICLE; CATALYSIS; CHELATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; GEOMETRY; ISOMERISM; LOW TEMPERATURE; MOLECULAR INTERACTION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034755306     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200111)2001:21<4067::AID-EJOC4067>3.0.CO;2-4     Document Type: Article

References (71)

1. L. S. Hegedus, Organische Synthese mit Übergangsmetallen, VCH, Weinheim, 1995.
2. For a detailed survey of palladium-catalyzed reactions, see: J. C. Malleron, J. C. Fiaud, J. Y. Legros, Handbook of Palladium-Catalyzed Organic Reactions, Academic Press, San Diego, 1997.
3. Reviews: [3a] S. A. Godleski, Comprehensive Organic Synthesis, vol 4 (Eds.: B. M. Trost, I. Fleming, M. F. Semmelhack) Pergamon, Oxford, 1991, pp 585-661.
4. [3b] T. Lübbers, P. Metz, Methoden Org. Chem (Houben Weyl) 1996, vol. E21, p. 2371-2473.
5. [3c] B. M. Trost, D. L. Van Vranken, Chem. Rev. 1996, 96, 395-422.
6. [3d] J. M. J. Williams, Synlett 1996, 705-710, and references cited therein.
7. [4a] I. Shimizu, T. Toyoda, T. Terashima, M. Oshima, H. Hasegawa, Synlett 1992, 301-302.
8. [4b] N. Greeves, J. S. Torode, Synthesis 1993, 1109-1112.
9. [4c] T. Hayashi, A. Ohno, S. Lu, Y. Matsumoto, E. Fukuyo, K. Yanagi, J. Am. Chem. Soc. 1994, 116, 4221-4226.
10. [4d] K. Hiroi, A. Hidaka, R. Sezaki, Y. Imamura, Chem. Pharm. Bull. 1997, 45, 769-777.
11. [5a] D. Ferroud, J. P. Genêt, R. Kiolle, Tetrahedron Lett. 1986, 27, 23-26.
12. [5b] J. C. Baldwin, J. M. J. Williams, R. P. Beckett, Tetrahedron: Asymmetry 1995, 6, 1515-1518.
13. [6a] M. Sawamura, H. Nagata, H. Sakamoto, Y. Ito, J. Am. Chem. Soc. 1992, 114, 2586-2592.
14. [6b] B. M. Trost, R. Radinov, E. M. Grenzer, J. Am. Chem. Soc. 1997, 119, 7879-7880.
15. [7a] B. M. Trost, E. Keinan, Tetrahedron Lett. 1980, 21, 2591-2594.
16. [7b] I. P. Beletskaya, J. Organomet. Chem. 1983, 250, 551-564.
17. [7c] B. M. Trost, C. R. Self, J. Org. Chem. 1984, 49, 468-473.
18. [7d] G. Q. Shi, X.-H. Huang, F.-J. Zhang, Tetrahedron Lett. 1995, 36, 6305-6308.
19. [7e] B. M. Trost, G. M. Schroeder, J. Am. Chem. Soc. 1999, 121, 6759-6760.
20. [8a] E. I. Negishi, R. A. John, J. Org. Chem. 1983, 48, 1098-4102.
21. [8b] N. Ono, I. Hamamoto, A. Kaji, Bull. Chem. Soc. Jpn. 1985, 58, 1863-1865.
22. M. Braun, F. Laicher, T. Meier, Angew. Chem. 2000, 112, 3637-3640;
23. Angew. Chem. Int. Ed. 2000, 39, 3494-3497.
24. [10a] L. S. Hegedus, W. H. Darlington, C. E. Russell, J. Org. Chem. 1980, 45, 5193-5196.
25. [10b] H. M. R. Hoffmann, A. R. Otte, A. Wilde, Angew. Chem. 1992, 104, 224-225;
26. Angew. Chem. Int. Ed. Engl. 1992, 31, 234-235.
27. [10c] A. R. Otte, A. Wilde, H. M. R. Hoffmann, Angew. Chem. 1994, 106, 1352-1354;
28. Angew. Chem. Int. Ed. Engl. 1994, 33, 1280-1282.
29. [10d] H. M. R. Hoffmann, A. R. Otte, A. Wilde, S. Menzer, D. J. Williams, Angew. Chem. 1995, 107, 73-76;
30. Angew. Chem. Int. Ed. Engl. 1995, 34, 100-103.
31. G. Consiglio, R. M. Waymouth, Chem. Rev. 1989, 89, 257-276.
32. P. Corradini, G. Maglio, A. Musco, G. Paiaro, J. Chem. Soc., Chem. Commun. 1966, 618-619.
33. [13a] J. W. Faller, M. E. Thomsen, M. J. Mattina, J. Am. Chem. Soc. 1971, 93, 2642-2653.
34. [13b] J. Lukas, J. E. Ramakers-Blom, T. G. Hewitt, J. J. De Boer, J. Organomet. Chem. 1972, 46, 167-177.
35. [14a] B. Åkermark, S. Hansson, A. Vitagliano, J. Am. Chem. Soc. 1990, 112, 4587-4588.
36. [14b] M. Sjögren, S. Hansson, P.-O. Norrby, B. Åkermark, M. E. Cucciolito, A. Vitagliano, Organometallics 1992, 11, 3954-3964.
37. For iridium-catalyzed reactions with retention of olefin geometry see: [15a] R. Takeuchi, M. Kashio, J. Am. Chem. Soc. 1998, 120, 8647-8655.
38. [15b] R. Takeuchi, N. Shiga, Org. Lett. 1999, 265-267.
39. [15c] R. Takeuchi, K. Tanabe, Angew. Chem. 2000, 112, 2051-2054;
40. Angew. Chem. Int. Ed. 2000, 39, 1975-1978.
41. [16a] S.-K. Kang, S.-G. Kim, J.-S. Lee, Tetrahedron: Asymmetry 1992, 3, 1139-1140.
42. [16b] T. Doi, A. Yanagisawa, M. Miyazawa, K. Yamamoto, Tetrahedron: Asymmetry 1995, 6, 389-392.
43. [16c] V. Michelet, J. P. Genêt, Bull. Soc. Chim. Fr. 1996, 133, 881-889.
44. [16d] B. M. Trost, M. A. Ceschi, B. König, Angew. Chem. 1997, 109, 1562-1564;
45. Angew. Chem. Int. Ed. Engl. 1997, 36, 1486-1489.
46. Reviews: [17a] U. Kazmaier, Amino Acids 1996, 11, 283-299.
47. [17b] U. Kazmaier, Liebigs Ann. Chem./Recueil 1997, 285-295.
48. [17c] U. Kazmaier, Recent Res. Dev. Org. Chem. 1998, 2, 351-358.
49. U. Kazmaier, Angew. Chem. 1994, 106, 1046;
50. Angew. Chem. Int. Ed. Engl. 1994, 33, 998.
51. [19a] U. Kazmaier, Tetrahedron 1994, 50, 12895-12902.
52. [19b] U. Kazmaier, J. Org. Chem. 1996, 61, 3694-3699.
53. [20a] F. L. Zumpe, U. Kazmaier, Synlett 1998, 1199-1200.
54. [20b] F. L. Zumpe, U. Kazmaier, Synthesis 1999, 1785-1791.
55. [20c] U. Kazmaier, S. Maier, F. L. Zumpe, Synlett 2000, 1523-1535.
56. [21a] U. Kazmaier, F. L. Zumpe, Angew. Chem. 1999, 111, 1572-1574;
57. Angew. Chem. Int. Ed. 1999, 38, 1468-1470;
58. [21b] U. Kazmaier, F. L. Zumpe, Angew. Chem. 2000, 112, 805-807;
59. Angew. Chem. Int. Ed. 2000, 39, 802-804.
60. K. Burgess, L. D. Jennings, J. Am. Chem. Soc. 1991, 113, 6129-6139.
61. T. Hayashi, A. Yamamoto, T. Hagihara, J. Org. Chem. 1986, 51, 723-727.
62. H. Lindlar, R. Dubuis, Org. Synth. Coll. Vol. V, 1973, 880-883.
63. [10]).
64. The configuration was determined by gas chromatography. The different stereoisomers required were synthesized by conversion of the (Z)-allyl carbonate and by Claisen rearrangement.
65. Y. Xu, B. Zhou, J. Org. Chem. 1987, 52, 974-977.
66. D. Seebach, A. K. Beck, B. Schmidt, Y.-M. Wang, Tetrahedron 1994, 50, 4363-4384.
67. J.-E. Bäckvall, R. E. Nordberg, D. Wilhelm, J. Am. Chem. Soc. 1985, 107, 6892-6898.
68. M. P. Balfe, J. Kenyon, D. Y. Waddan, J. Chem. Soc. 1954, 1366-1372.
69. H. Neumann, D. Seebach, Chem. Ber. 1978, 111, 2785-2812.
70. J. McKew, M. J. Kurth, J. Org. Chem. 1993, 58, 4589-4595.
71. I. Fleming, K. Takaki, A. P. Thomas, J. Chem. Soc., Perkin Trans. 1 1987, 2269-2273.