Application of the chelate-enolate Claisen rearrangement to the synthesis of γ,δ-unsaturated amino acids

Liebigs Annales

Volumn , Issue 2, 1997, Pages 285-295

  Kazmaier, Uli ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Amino acids, polyhyroxylated; Amino acids, unsaturated; Asymmetric Claisen rearrangement; Chelate enolate Claisen rearrangement

Indexed keywords

EID: 33748837205     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199719970203     Document Type: Short Survey

References (106)

1. [1a] U. Cramer, A. G. Rehfeldt, F. Spencer, Biochemistry 1980, 19, 3074.
2. [1b] J. Edelson, J. D. Fissekis, C. G. Skinner, W. Shive, J. Am. Chem. Soc. 1958, 80, 2698.
3. K. Katagiri, K. Tori, Y. Kimura, T. Yoshida, T. Nagasaki, H. Minato, J. Med. Chem. 1967, 10, 1149.
4. [3a] P. A. Bartlett, D. J. Tanzella, J. F. Barstow, Tetrahedron Lett. 1982, 23, 619.
5. [3b] Y. Ohfune, N. Kurokawa, Tetrahedron Lett. 1985, 26, 5307.
6. [3c] N. Kurokawa, Y. Ohfune, J. Am. Chem. Soc. 1986, 108, 6041.
7. [3d] H. Baumann, R. O. Duthaler, Helv. Chim. Acta 1988, 71, 1025.
8. [3e] Q. B. Broxterman, B. Kaptein, J. Kamphuis, H. E. Schoemaker, J. Org. Chem. 1992, 57, 6286.
9. [4a] O. Achmatowicz, Jr., M. Pietraszkiewicz, J. Chem. Soc., Perkin Trans. 1 1981, 2680.
10. [4b] D. M. Tschaen, S. M. Weinreb, Tetrahedron Lett. 1982, 23, 3015.
11. [4c] D. M. Tschaen, E. Turos, S. M. Weinreb, J. Org. Chem. 1984, 49, 5058.
12. [5a] R. M. Williams, P. J. Sinclair, D. Zhai, D. Chen, J. Am. Chem. Soc. 1988, 110, 1547.
13. [5b] C. J. Easton, I. M. Scharfbillig, J. Org. Chem. 1990, 55, 384.
14. [5c] E. C. Roos, H. H. Mooiweer, H. Hiemstra, W. N. Speckamp, B. Kaptein, W. H. J. Boesten, J. Kamphuis, J. Org. Chem. 1992, 57, 6769.
15. [5d] E. C. Roos, M. C. Lopez, M. A. Brook, H. Hiemstra, W. N. Speckamp, B. Kaptein, J. Kamphuis, H. E. Schoemaker, J. Org. Chem. 1993, 58, 3259.
16. R. M. Williams, Synthesis of Optically Active α-Amino Acids, Vol. 7 of Organic Chemistry Series, J. E. Baldwin, P. D. Magnus (Eds.), Pergamon Press, Oxford 1989.
17. [7a] B. Kübel, G. Höfle, W. Steglich, Angew. Chem. 1975, 87, 64;
18. Angew. Chem. Int. Ed. Engl. 1975, 14, 58.
19. [7b] N. Engel, B. Kübel, W. Steglich, Angew. Chem. 1977, 89, 408;
20. Angew. Chem. Int. Ed. Engl. 1977, 16, 394.
21. [8a] J. Fischer, C. Kilpert, U. Klein, W. Steglich, Tetrahedron 1986, 42, 2063.
22. [8b] K. Burger, K. Geith, K. Gaa, Angew. Chem. 1988, 100, 860;
23. Angew. Chem. Int. Ed. Engl. 1988, 27, 848.
24. [8c] L. Colombo, G. Casiraghi, A. Pittalis, G. Rassu, J. Org. Chem. 1991, 56, 3897.
25. [8d] M. W. Holladay, A. M. Nadzan, J. Org. Chem. 1991, 56, 3900.
26. R. E. Ireland, R. H. Mueller, J. Am. Chem. Soc. 1972, 94, 5897.
27. P. A. Bartlett, J. F. Barstow, J. Org. Chem. 1982, 47, 3933.
28. [11a] U. Kazmaier, R. Grandel, Synlett 1995, 945.
29. [11b] R. Grandel, U. Kazmaier, B. Nuber, Liebigs Ann. 1996, 1143.
30. For reviews on Claisen and related sigmatropic rearrangements see: [12a] P. A. Bartlett, Tetrahedron 1980, 36, 3.
31. [12b] F. E. Ziegler, Chem. Rev. 1988, 88, 1423.
32. [12c] S. Blechert, Synthesis 1989, 71.
33. [12d] P. Wipf in Comprehensive Organic Synthesis, Vol. 5, B. M. Trost, I. Fleming (Eds.), Pergamon Press, New York, 1991, 827.
34. [12e] H.-J. Altenbach in Organic Synthesis Highlights, J. Mulzer, H.-J. Altenbach, M. Braun, K. Krolin, H.-U. Reissig (Eds.), VCH, Weinheim, 1991, 111, 116.
35. [12f] S. Pereira, M. Srebnik, Aldrichimica Acta 1993, 26, 17.
36. [12g] H. Frauenrath in Houben-Weyl E 21d, G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann (Eds.), Thieme, Stuttgart, 1995, 3301.
37. [13a] P. A. Bartlett, D. J. Tanzella, J. F. Barstow, J. Org. Chem. 1982, 47, 3941.
38. [13b] S. D. Burke, W. F. Fobare, G. J. Pacofsky, J. Org. Chem. 1983, 48, 5221.
39. [13c] J. Kallmerten, T. J. Gould, J. Org. Chem. 1986, 51, 1153.
40. U. Kazmaier, Angew. Chem. 1994, 106, 1046;
41. Angew. Chem. Int. Ed. Engl. 1994, 33, 998.
42. U. Kazmaier, Tetrahedron 1994, 50, 12895.
43. For reviews on asymmetric syntheses of quaternary carbon centers see: [16a] S. F. Martin, Tetrahedron 1980, 36, 419.
44. [16b] K. Fuji, Chem. Rev. 1993, 93, 2037.
45. [17a] S. Takano, M. Akiyama, K. Ogasawara, J. Chem. Soc., Chem. Commun. 1984, 770.
46. [17b] Y. Ito, N. Higuchi, M. Murakami, Tetrahedron Lett. 1988, 5151.
47. [18a] U. Kazmaier, S. Maier, J. Chem. Soc., Chem. Commun. 1995, 1991.
48. [18b] U. Kazmaier, S. Maier, Tetrahedron 1996, 52, 941.
49. M. Gander-Coquoz, D. Seebach, Helv. Chim. Acta 1988, 71, 224.
50. U. Schöllkopf, R. Lonsky, Synthesis 1983, 675.
51. T. Weber, R. Aeschimann, T. Maetzke, D. Seebach, Helv. Chim. Acta 1986, 69, 1365.
52. [22a] A. L. Maycock, S. D. Aster, A. A. Patchett, Developments in Biochemistry 1979, 6, 115.
53. [22b] C. Danzin, P. Casara, N. Claverie, B. W. Metcalf, J. Med. Chem. 1981, 24, 16.
54. U. Schmidt, A. Lieberknecht, J. Wild, Synthesis 1984, 53.
55. U. Kazmaier, Tetrahedron Lett. 1996, 37, 5351.
56. U. Schmidt, H. Griesser, V. Leitenberger, A. Lieberknecht, R. Mangold, R. Meyer, B. Riedl, Synthesis 1992, 487.
57. J. E. Baldwin, J. Chem. Soc., Chem. Commun. 1976, 734ff.
58. R. F. Heck in Palladium Reagents in Organic Syntheses, Academic Press, London, 1985.
59. G. T. Crisp, P. T. Glink, Tetrahedron 1992, 48, 3541.
60. [29a] H. Gehring, R. R. Rando, P. Christen, Biochemistry 1977, 16, 4832.
61. [29b] J. J. Likos, H. Ueno, R. W. Fieldhaus, D. E. Metzler, Biochemistry 1982, 21, 4377.
62. A. L. Castelhano, D. H. Pliura, G. J. Taylor, K. C. Hsieh, A. Krantz, J. Am. Chem. Soc. 1984, 106, 2734.
63. D. K. Black, S. R. Landor, J. Chem. Soc. (C), 1968, 283.
64. G. B. Bennett, Synthesis 1977, 589.
65. [33a] B. Kübel; P. Gruber, R. Hurnaus, W. Steglich, Chem. Ber. 1979, 112, 128.
66. [33b] J. Fischer, C. Kilpert, U. Klein, W. Steglich, Tetrahedron 1986, 42, 2063.
67. A. L. Castelhano, S. Horne, G. J. Taylor, R. Billedeau, A. Krantz, Tetrahedron 1988, 44, 5451.
68. U. Kazmaier, C. H. Görbitz, Synthesis in press.
69. Determined by X-Ray-Structure: C. H. Görbitz, U. Kazmaier, unpublished results.
70. D. Hoppe, C. Gonschorrek, E. Egert, D. Schmidt, Angew. Chem. 1985, 97, 706;
71. Angew. Chem. Int. Ed. Engl. 1985, 24, 700.
72. S. Masamune, S. A. Ali, D. L. Snitman, D. S. Garvey, Angew. Chem. 1980, 92, 573;
73. Angew. Chem. Int. Ed. Engl. 1980, 19, 557.
74. For a recent review on asymmetric Claisen rearrangement see: D. Enders, M. Knopp, R. Schiffers, Tetrahedron: Asymmetry 1996, 7, 1847, and cited references.
75. U. Kazmaier, C. Schneider, Synlett in press.
76. U. Kazmaier, C. Schneider unpublished results.
77. For reviews see:[42a] D. Seebach, Angew. Chem. 1988, 100, 1685;
78. Angew. Chem. Int. Ed. 1988, 27, 1624.
79. [42b] D. Seebach, Aldrichim. Acta 1992, 25, 59.
80. D. Seebach, H. Bossler, H. Gründler, S. Shoda, R. Wenger, Helv. Chim. Acta 1991, 74, 197.
81. S. A. Miller, S. L. Griffiths, D. Seebach, Helv. Chim. Acta 1993, 76, 563.
82. D. Seebach, A. K. Beck, H. G. Bossler, C. Gerber, S. Y. Ko, C. W. Murtiashaw, R. Naef, S. Shoda, A. Thaler, M. Krieger, R. Wenger, Helv. Chim. Acta 1993, 76, 1564.
83. M. T. Reetz, J. Kanand, N. Griebenow, K. Harms, Angew. Chem. 1992, 104, 1638;
84. Angew. Chem. Int. Ed. Engl. 1992, 31, 1626.
85. U. Kazmaier, J. Org. Chem. 1994, 59, 6667.
86. [48a] L. E. Overman, C. B. Campbell, J. Org. Chem. 1976, 41, 3338.
87. [48b] L. E. Overman, C. B. Campbell, F. M. Knoll, J. Am. Chem. Soc. 1978, 100, 4822.
88. [48c] L. E. Overman, Angew. Chem. 1984, 96, 565;
89. Angew. Chem. Int. Ed. Engl. 1984, 23, 579.
90. See also: [48d] R. P. Lutz, Chem. Rev. 1984, 84, 205.
91. For mechanistic studies see: [49a] L. E. Overman, E. J. Jacobsen, J. Am. Chem. Soc. 1982, 104, 7225.
92. [49b] T. G. Schenck, B. Bosnich, J. Am. Chem. Soc. 1985, 107, 2058.
93. [49c] L. E. Overman, A. F. Renaldo, J. Am. Chem. Soc. 1990, 112, 3945.
94. H. Sigel, B. Martin, Chem. Rev. 1982, 82, 385.
95. For Pd(0)-catalyzed allylic alkylation of amino ester Schiff bases see: [51a] D. Ferroud, J. P. Genet, R. Kiolle, Tetrahedron Lett. 1986, 27, 23.
96. [51b] J. P. Genet, D. Ferroud, S. Juge, J. R. Montes, Tetrahedron Lett. 1986, 27, 4573.
97. [51c] J. P. Genet, S. Juge, J. Ruiz-Montes, J. M. Gaudin, J. Chem. Soc. Chem. Commun. 1988, 718.
98. A. van der Werf, R. M. Kellogg, Tetrahedron Lett. 1988, 29, 4981.
99. [53a] K. Maruoka, H. Banno, H. Yamamoto, J. Am. Chem. Soc. 1990, 112, 7791.
100. [53b] K. Maruoka, S. Saito, H. Yamamoto, J. Am. Chem. Soc. 1995, 117, 1165.
101. [54a] E. J. Corey, D. Lee, J. Am. Chem. Soc. 1991, 113, 4026.
102. [54b] E. J. Corey, B. E. Roberts, B. R. Dixon, J. Am. Chem. Soc. 1995, 117, 193.
103. U. Kazmaier, A. Krebs, Angew. Chem. 1995, 107, 2213;
104. Angew. Chem. Int. Ed. Engl. 1995, 34, 2012.
105. I. Ojima in Catalytic Asymmetric Synthesis, VCH, New York, 1993.
106. A. Krebs, U. Kazmaier, Tetrahedron Lett., in press.