Synthesis of allenic amino acids via chelate-controlled ester enolate Claisen rearrangement

Synthesis

Volumn , Issue 12, 1996, Pages 1489-1493

  Kazmaier, Uli ^b   Görbitz, Carl Henrik ^b  

^a UNIVERSITY OF HEIDELBERG   (Germany)

^b NONE

Author keywords

allene; amino acids; chelate enolate; Claisen rearrangement; propargylic esters

Indexed keywords

ALLENE DERIVATIVE; AMINO ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0030457755     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4413     Document Type: Article

References (37)

1. Williams, R. M. Synthesis of Optically Active α-Amino Acids, Vol 7 of Organic Chemistry Series; Baldwin, J. E.; Magnus, P. D. Eds.; Pergamon: Oxford, 1989.
2. Walsh, C. Tetrahedron 1982, 36, 871. Carpino, P. A.; Peevey, R. M.; Pratt, D. V.; Tenge, B. J.; Hopkins, P. B. J. Org. Chem. 1986, 51, 2734. Angst, C. Pure Appl. Chem. 1987, 59, 373.
3. Walsh, C. Tetrahedron 1982, 36, 871. Carpino, P. A.; Peevey, R. M.; Pratt, D. V.; Tenge, B. J.; Hopkins, P. B. J. Org. Chem. 1986, 51, 2734. Angst, C. Pure Appl. Chem. 1987, 59, 373.
4. Walsh, C. Tetrahedron 1982, 36, 871. Carpino, P. A.; Peevey, R. M.; Pratt, D. V.; Tenge, B. J.; Hopkins, P. B. J. Org. Chem. 1986, 51, 2734. Angst, C. Pure Appl. Chem. 1987, 59, 373.
5. Riberau-Gayon, G.; Danzin, C.; Palfreyman, M. G.; Aubry, M.; Wagner, J.; Metcalf, B. W.; Jung, M. J. J. Biochem. Pharmacol. 1979, 28, 1331.
6. Gehring, H.; Rando, R. R.; Christen, P. Biochemistry 1977, 16, 4832. Likos, J. J.; Ueno, H.; Fieldhaus, R. W; Metzler, D. E. Biochemistry 1982, 21, 4377.
7. Gehring, H.; Rando, R. R.; Christen, P. Biochemistry 1977, 16, 4832. Likos, J. J.; Ueno, H.; Fieldhaus, R. W; Metzler, D. E. Biochemistry 1982, 21, 4377.
8. Castelhano, A. L.; Pliura, D. H.; Taylor, G. J.; Hsieh, K. C.; Krantz, A. J. Am. Chem. Soc. 1984, 106, 2734.
9. Black, D. K.; Landor, S. R. J. Chem. Soc (C), 1968, 283.
10. For reviews on sigmatropic rearrangements see: Ziegler, F. E. Chem. Rev. 1988, 88, 1423. Blechert, S. Synthesis 1989, 71. Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds.; Pergamon: New York, 1991, Vol. 5, p 827. Altenbach, H.-J. In Organic Synthesis Highlights; Mulzer, J.; Altenbach, H.-J.; Braun, M.; Krohn, K.; Reissig, H.-U. Eds.; VCH: Weinheim, 1991, pp 111, 116. Pereira, S.; Srebnik, M. Aldrichimica Acta 1993, 26, 17. Frauenrath, H. in Houben Weyl Vol. E21d (Stereoselective Synthesis); Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E. Eds.; Thieme: Stuttgart, 1995, p 3301.
11. For reviews on sigmatropic rearrangements see: Ziegler, F. E. Chem. Rev. 1988, 88, 1423. Blechert, S. Synthesis 1989, 71. Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds.; Pergamon: New York, 1991, Vol. 5, p 827. Altenbach, H.-J. In Organic Synthesis Highlights; Mulzer, J.; Altenbach, H.-J.; Braun, M.; Krohn, K.; Reissig, H.-U. Eds.; VCH: Weinheim, 1991, pp 111, 116. Pereira, S.; Srebnik, M. Aldrichimica Acta 1993, 26, 17. Frauenrath, H. in Houben Weyl Vol. E21d (Stereoselective Synthesis); Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E. Eds.; Thieme: Stuttgart, 1995, p 3301.
12. For reviews on sigmatropic rearrangements see: Ziegler, F. E. Chem. Rev. 1988, 88, 1423. Blechert, S. Synthesis 1989, 71. Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds.; Pergamon: New York, 1991, Vol. 5, p 827. Altenbach, H.-J. In Organic Synthesis Highlights; Mulzer, J.; Altenbach, H.-J.; Braun, M.; Krohn, K.; Reissig, H.-U. Eds.; VCH: Weinheim, 1991, pp 111, 116. Pereira, S.; Srebnik, M. Aldrichimica Acta 1993, 26, 17. Frauenrath, H. in Houben Weyl Vol. E21d (Stereoselective Synthesis); Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E. Eds.; Thieme: Stuttgart, 1995, p 3301.
13. For reviews on sigmatropic rearrangements see: Ziegler, F. E. Chem. Rev. 1988, 88, 1423. Blechert, S. Synthesis 1989, 71. Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds.; Pergamon: New York, 1991, Vol. 5, p 827. Altenbach, H.-J. In Organic Synthesis Highlights; Mulzer, J.; Altenbach, H.-J.; Braun, M.; Krohn, K.; Reissig, H.-U. Eds.; VCH: Weinheim, 1991, pp 111, 116. Pereira, S.; Srebnik, M. Aldrichimica Acta 1993, 26, 17. Frauenrath, H. in Houben Weyl Vol. E21d (Stereoselective Synthesis); Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E. Eds.; Thieme: Stuttgart, 1995, p 3301.
14. For reviews on sigmatropic rearrangements see: Ziegler, F. E. Chem. Rev. 1988, 88, 1423. Blechert, S. Synthesis 1989, 71. Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds.; Pergamon: New York, 1991, Vol. 5, p 827. Altenbach, H.-J. In Organic Synthesis Highlights; Mulzer, J.; Altenbach, H.-J.; Braun, M.; Krohn, K.; Reissig, H.-U. Eds.; VCH: Weinheim, 1991, pp 111, 116. Pereira, S.; Srebnik, M. Aldrichimica Acta 1993, 26, 17. Frauenrath, H. in Houben Weyl Vol. E21d (Stereoselective Synthesis); Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E. Eds.; Thieme: Stuttgart, 1995, p 3301.
15. For reviews on sigmatropic rearrangements see: Ziegler, F. E. Chem. Rev. 1988, 88, 1423. Blechert, S. Synthesis 1989, 71. Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds.; Pergamon: New York, 1991, Vol. 5, p 827. Altenbach, H.-J. In Organic Synthesis Highlights; Mulzer, J.; Altenbach, H.-J.; Braun, M.; Krohn, K.; Reissig, H.-U. Eds.; VCH: Weinheim, 1991, pp 111, 116. Pereira, S.; Srebnik, M. Aldrichimica Acta 1993, 26, 17. Frauenrath, H. in Houben Weyl Vol. E21d (Stereoselective Synthesis); Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E. Eds.; Thieme: Stuttgart, 1995, p 3301.
16. Bennett, G. B. Synthesis 1977, 589.
17. Kübel, B.; Gruber, P.; Hurnaus, R.; Steglich, W. Chem. Ber. 1979, 112, 128. Fischer, J.; Kilpert, C.; Klein, U.; Steglich, W. Tetrahedron 1986, 42, 2063.
18. Kübel, B.; Gruber, P.; Hurnaus, R.; Steglich, W. Chem. Ber. 1979, 112, 128. Fischer, J.; Kilpert, C.; Klein, U.; Steglich, W. Tetrahedron 1986, 42, 2063.
19. Castelhano, A. L.; Horne, S., Taylor, G. J.; Billedeau, R.; Krantz, A. Tetrahedron 1988, 44, 5451.
20. Ireland, R. E.; Mueller, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976, 98, 2868.
21. Bartlett, P. A.; Barstow, J. F. J. Org. Chem. 1982, 47, 3933.
22. Kazmaier, U. Angew. Chem. 1994, 106, 1096. Angew. Chem., Int. Ed. Engl. 1994, 33, 998.
23. Kazmaier, U. Angew. Chem. 1994, 106, 1096. Angew. Chem., Int. Ed. Engl. 1994, 33, 998.
24. This is in contrast to the observation made in aza-Claisen rearrangements of N-acylglycine amides. See: Tsunoda, T.; Tatsuki, S.; Shiraishi, Y.; Akasaka, M.; Ito, S. Tetrahedtron Lett. 1993, 34, 3297.
25. Kazmaier, U. Tetrahedron 1994, 50, 12895.
26. Kazmaier, U. J. Org. Chem. 1994, 59, 6667.
27. Kazmaier, U.; Krebs, A. Angew. Chem. 1995, 107, 2213; Angew. Chem., Int. Ed. Engl. 1995, 34, 2012.
28. Kazmaier, U.; Krebs, A. Angew. Chem. 1995, 107, 2213; Angew. Chem., Int. Ed. Engl. 1995, 34, 2012.
29. Neises, B.; Steglich, W. Angew. Chem. 1978, 90, 556; Angew. Chem., Int. Ed. Engl. 1978, 17, 522.
30. Neises, B.; Steglich, W. Angew. Chem. 1978, 90, 556; Angew. Chem., Int. Ed. Engl. 1978, 17, 522.
31. For comparable rearrangements see: Fujisawa, T.; Maehata, E.; Kohama, H.; Sato, T. Chem. Lett. 1985, 1457. Henderson, M. A.; Heathcock, C. H. J. Org. Chem. 1988, 53, 4736.
32. For comparable rearrangements see: Fujisawa, T.; Maehata, E.; Kohama, H.; Sato, T. Chem. Lett. 1985, 1457. Henderson, M. A.; Heathcock, C. H. J. Org. Chem. 1988, 53, 4736.
33. Further details of the X-ray structure determination may be obtained through the Fachinformationszentrum Karlsruhe, D-76344 Eggenstein-Leopoldshafen, Germany on quoting the depository number CSD-405551.
34. Hoppe, D.; Gonschorrek, C.; Egert, E.; Schmidt, D. Angew. Chem. 1985, 97, 706; Angew. Chem., Int. Ed. Engl. 1985, 24, 700.
35. Hoppe, D.; Gonschorrek, C.; Egert, E.; Schmidt, D. Angew. Chem. 1985, 97, 706; Angew. Chem., Int. Ed. Engl. 1985, 24, 700.
36. Masamune, S.; Ali, S. A.; Snitman, D. L.; Garvey, D. S. Angew. Chem. 1980, 92, 573; Angew. Chem., Int. Ed. Engl. 1980, 19, 654.
37. Masamune, S.; Ali, S. A.; Snitman, D. L.; Garvey, D. S. Angew. Chem. 1980, 92, 573; Angew. Chem., Int. Ed. Engl. 1980, 19, 654.