Synthesis of quaternary amino acids containing β,γ- and well as γ,δ-unsaturated side chains via chelate-enolate Claisen rearrangement

Tetrahedron Letters

Volumn 37, Issue 30, 1996, Pages 5351-5354

  Kazmaier, Uli ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030598033     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01104-5     Document Type: Article

References (40)

1. 1. Heimgartner, H. Angew. Chem. 1991, 103, 271; Angew. Chem. Int. Ed. Engl. 1991, 30, 238.
2. 1. Heimgartner, H. Angew. Chem. 1991, 103, 271; Angew. Chem. Int. Ed. Engl. 1991, 30, 238.
3. 2. Walsh, J. J.; Metzler, D. E.; Powell, D.; Jacobsen, R. A. J. Am. Chem. Soc. 1980, 102, 130. Ramalingam, K.; Woodward, R. W. Tetrahedron Lett. 1985, 26, 1135. Tendler, S. J. B.; Threadgill, M. D.; Tisdale, M. J. J. Chem. Soc. Perkin Trans. I 1987, 2617.
4. 2. Walsh, J. J.; Metzler, D. E.; Powell, D.; Jacobsen, R. A. J. Am. Chem. Soc. 1980, 102, 130. Ramalingam, K.; Woodward, R. W. Tetrahedron Lett. 1985, 26, 1135. Tendler, S. J. B.; Threadgill, M. D.; Tisdale, M. J. J. Chem. Soc. Perkin Trans. I 1987, 2617.
5. 2. Walsh, J. J.; Metzler, D. E.; Powell, D.; Jacobsen, R. A. J. Am. Chem. Soc. 1980, 102, 130. Ramalingam, K.; Woodward, R. W. Tetrahedron Lett. 1985, 26, 1135. Tendler, S. J. B.; Threadgill, M. D.; Tisdale, M. J. J. Chem. Soc. Perkin Trans. I 1987, 2617.
6. 3. Maycock, A. L.; Aster, S. D.; Patchett, A. A. Developments in Biochemistry 1979, 6, 115. Danzin, C.; Casara, P.; Claverie, N.; Metcalf, B. W. J. Med. Chem. 1981, 24, 16.
7. 3. Maycock, A. L.; Aster, S. D.; Patchett, A. A. Developments in Biochemistry 1979, 6, 115. Danzin, C.; Casara, P.; Claverie, N.; Metcalf, B. W. J. Med. Chem. 1981, 24, 16.
8. 4. For general informations see: Williams, R. M. Synthesis of Optically Active α-Amino Acids, Vol. 7 of Organic Chemistry Series; Baldwin, J. E.; Magnus P. D. (Eds.); Pergamon Press, Oxford 1989.
9. 5. Berkowitz, D. B.; Pumphrey, J. A.; Shen, Q. Tetrahedron Lett. 1994, 35, 8743. Mulzer, J.; Funk, G. Synthesis, 1995, 101.
10. 5. Berkowitz, D. B.; Pumphrey, J. A.; Shen, Q. Tetrahedron Lett. 1994, 35, 8743. Mulzer, J.; Funk, G. Synthesis, 1995, 101.
11. 6. Metcalf, B. W.; Jund, K. Tetrahedron Lett. 1977, 3689. Steglich, W.; Wegmann, H. Synthesis 1980, 481. Bey, P.; Vevert, J. P. J. Org. Chem. 1980, 45, 3249. Colson, P.-J.; Hegedus, L. S.; J. Org. Chem. 1993, 58, 5918.
12. 6. Metcalf, B. W.; Jund, K. Tetrahedron Lett. 1977, 3689. Steglich, W.; Wegmann, H. Synthesis 1980, 481. Bey, P.; Vevert, J. P. J. Org. Chem. 1980, 45, 3249. Colson, P.-J.; Hegedus, L. S.; J. Org. Chem. 1993, 58, 5918.
13. 6. Metcalf, B. W.; Jund, K. Tetrahedron Lett. 1977, 3689. Steglich, W.; Wegmann, H. Synthesis 1980, 481. Bey, P.; Vevert, J. P. J. Org. Chem. 1980, 45, 3249. Colson, P.-J.; Hegedus, L. S.; J. Org. Chem. 1993, 58, 5918.
14. 6. Metcalf, B. W.; Jund, K. Tetrahedron Lett. 1977, 3689. Steglich, W.; Wegmann, H. Synthesis 1980, 481. Bey, P.; Vevert, J. P. J. Org. Chem. 1980, 45, 3249. Colson, P.-J.; Hegedus, L. S.; J. Org. Chem. 1993, 58, 5918.
15. 7. Pedersen, M. L.; Berkowitz, D. B. J. Org. Chem. 1993, 58, 6966.
16. 8. Greenlee, W. J.; Taub, D.; Patchett, A. A. Tetrahedron Lett. 1978, 3999. Hoppe, I.; Schöllkopf, U. Synthesis 1981, 646. Seebach, D.; Bürger, H. M.; Schickli, C. P. Liebigs Ann. Chem. 1991, 669.
17. 8. Greenlee, W. J.; Taub, D.; Patchett, A. A. Tetrahedron Lett. 1978, 3999. Hoppe, I.; Schöllkopf, U. Synthesis 1981, 646. Seebach, D.; Bürger, H. M.; Schickli, C. P. Liebigs Ann. Chem. 1991, 669.
18. 8. Greenlee, W. J.; Taub, D.; Patchett, A. A. Tetrahedron Lett. 1978, 3999. Hoppe, I.; Schöllkopf, U. Synthesis 1981, 646. Seebach, D.; Bürger, H. M.; Schickli, C. P. Liebigs Ann. Chem. 1991, 669.
19. 9. Katagiri, K.; Tori, K.; Kimura, Y.; Yoshida, T.; Nagasaki, T.; Minato, H. J. Med. Chem. 1967, 10, 1149. Cramer, U.; Rehfeldt, A. G.; Spener, F. Biochemistry 1980, 19, 3074. Tsubotani, S.; Funabashi, Y.; Takamoto, M.; Hakoda, S.; Harada, S. Tetrahedron 1991, 47, 8079.
20. 9. Katagiri, K.; Tori, K.; Kimura, Y.; Yoshida, T.; Nagasaki, T.; Minato, H. J. Med. Chem. 1967, 10, 1149. Cramer, U.; Rehfeldt, A. G.; Spener, F. Biochemistry 1980, 19, 3074. Tsubotani, S.; Funabashi, Y.; Takamoto, M.; Hakoda, S.; Harada, S. Tetrahedron 1991, 47, 8079.
21. 9. Katagiri, K.; Tori, K.; Kimura, Y.; Yoshida, T.; Nagasaki, T.; Minato, H. J. Med. Chem. 1967, 10, 1149. Cramer, U.; Rehfeldt, A. G.; Spener, F. Biochemistry 1980, 19, 3074. Tsubotani, S.; Funabashi, Y.; Takamoto, M.; Hakoda, S.; Harada, S. Tetrahedron 1991, 47, 8079.
22. 10. Bartlett, P. A.; Tanzella, D. J.; Barstow, J. F. Tetrahedron Lett. 1982, 23, 619. Ohfune, Y.; Kurokawa, N. Tetrahedron Lett. 1985, 26, 5307. Kurokawa, N.; Ohfune, Y. J. Am. Chem. Soc. 1986, 108, 6041. Baumann, H.; Duthaler, R. O.; Helv. Chim. Acta 1988, 71, 1025. Broxterman, Q. B.; Kaptein, B.; Kamphuis, J.; Schoemaker, H. E. J. Org. Chem. 1992, 57, 6286.
23. 10. Bartlett, P. A.; Tanzella, D. J.; Barstow, J. F. Tetrahedron Lett. 1982, 23, 619. Ohfune, Y.; Kurokawa, N. Tetrahedron Lett. 1985, 26, 5307. Kurokawa, N.; Ohfune, Y. J. Am. Chem. Soc. 1986, 108, 6041. Baumann, H.; Duthaler, R. O.; Helv. Chim. Acta 1988, 71, 1025. Broxterman, Q. B.; Kaptein, B.; Kamphuis, J.; Schoemaker, H. E. J. Org. Chem. 1992, 57, 6286.
24. 10. Bartlett, P. A.; Tanzella, D. J.; Barstow, J. F. Tetrahedron Lett. 1982, 23, 619. Ohfune, Y.; Kurokawa, N. Tetrahedron Lett. 1985, 26, 5307. Kurokawa, N.; Ohfune, Y. J. Am. Chem. Soc. 1986, 108, 6041. Baumann, H.; Duthaler, R. O.; Helv. Chim. Acta 1988, 71, 1025. Broxterman, Q. B.; Kaptein, B.; Kamphuis, J.; Schoemaker, H. E. J. Org. Chem. 1992, 57, 6286.
25. 10. Bartlett, P. A.; Tanzella, D. J.; Barstow, J. F. Tetrahedron Lett. 1982, 23, 619. Ohfune, Y.; Kurokawa, N. Tetrahedron Lett. 1985, 26, 5307. Kurokawa, N.; Ohfune, Y. J. Am. Chem. Soc. 1986, 108, 6041. Baumann, H.; Duthaler, R. O.; Helv. Chim. Acta 1988, 71, 1025. Broxterman, Q. B.; Kaptein, B.; Kamphuis, J.; Schoemaker, H. E. J. Org. Chem. 1992, 57, 6286.
26. 10. Bartlett, P. A.; Tanzella, D. J.; Barstow, J. F. Tetrahedron Lett. 1982, 23, 619. Ohfune, Y.; Kurokawa, N. Tetrahedron Lett. 1985, 26, 5307. Kurokawa, N.; Ohfune, Y. J. Am. Chem. Soc. 1986, 108, 6041. Baumann, H.; Duthaler, R. O.; Helv. Chim. Acta 1988, 71, 1025. Broxterman, Q. B.; Kaptein, B.; Kamphuis, J.; Schoemaker, H. E. J. Org. Chem. 1992, 57, 6286.
27. 11. Kazmaier, U. Angew. Chem. 1994, 106, 1096; Angew. Chem., Int. Ed. Engl. 1994, 33, 998.
28. 11. Kazmaier, U. Angew. Chem. 1994, 106, 1096; Angew. Chem., Int. Ed. Engl. 1994, 33, 998.
29. 12. Kazmaier, U. Synlett 1995, 1138. Kazmaier, U.; Maier, S. Tetrahedron 1996, 52, 941.
30. 12. Kazmaier, U. Synlett 1995, 1138. Kazmaier, U.; Maier, S. Tetrahedron 1996, 52, 941.
31. 13. Kazmaier, U. J. Org. Chem. 1994, 59, 6667.
32. 14. Schmidt, U.; Lieberknecht, A.; Wild, J. Synthesis 1984, 53.
33. 15. Schmidt, U.; Griesser, H.; Leitenberger, V.; Lieberknecht, A., Mangold, R.; Meyer, R.; Riedl, B. Synthesis 1992, 487
34. 3) δ 172.8, 156.1, 137.9, 132.3, 128.4, 113.5, 65.7, 51.8, 47.2, 45.0, 21.5, 21.0, 17.9, 15.6.
35. 17. For comparable iodolactonizations see: Bartlett, P. A.; Barstow, J. F. J. Org. Chem. 1982, 47, 3933. Guillerm, G. Syn. Commun. 1995, 25, 877.
36. 17. For comparable iodolactonizations see: Bartlett, P. A.; Barstow, J. F. J. Org. Chem. 1982, 47, 3933. Guillerm, G. Syn. Commun. 1995, 25, 877.
37. 18. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734 ff.
38. 19. Heck, R. F. Palladium Reagents in Organic Syntheses, Academic Press, London, 1985.
39. 20. Crisp, G. F.; Glink, P. T. Tetrahedron, 1992, 48, 3541.
40. 3) δ 173.0, 156.0, 136.8, 134.7, 132.5, 130.3, 129.2, 129.0, 128.8, 126.6, 65.6, 51.9, 47.6, 45.2, 21.4, 21.1, 17.9, 15.8.