Asymmetric α-alkylation of α-amino esters using pyridoxal derivatives having a chiral ansa-structure and a chiral ionophore function: A novel example of double asymmetric induction

Tetrahedron

Volumn 56, Issue 27, 2000, Pages 4691-4700

  Miyashita, Kazuyuki ^a   Miyabe, Hideto ^a   Tai, Kuninori ^a   Iwaki, Hiroshi ^a   Imanishi, Takeshi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Alkylation; Amino acids and derivatives; Ansa compounds; Asymmetric reactions; Pyridines

Indexed keywords

ESTER; IMINE; IONOPHORE; LITHIUM ION; PYRIDOXAL;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0034733671     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00392-6     Document Type: Article

References (28)

1. For example: Walsh, J. J.; Metzler, D. E.; Powell, D.; Jacobson, R. A. J. Am. Chem. Soc. 1980, 102, 7136-7138; Kiick, D. M.; Cook, P. F. Biochemistry 1983, 22, 375-382; Saari, W. S.; Halczenko, W.; Cochran, D. W.; Dobrinska, M. R.; Vincek, W. C.; Titus, D. C.; Gaul, S. L.; Sweet, C. S. J. Med. Chem. 1984, 27, 713-717; Yamashita, T.; Iijima, M.; Nakamura, H.; Isshiki, K.; Naganawa, H.; Hattori, S.; Hamada, M.; Ishizuka, M.; Takeuchi, T. J. Antibiot. 1991, 44, 557-559; Horn, W. S.; Smith, J. L.; Bills, G. F.; Raghoobar, S. L.; Helms, G. L.; Kurtz, M. B.; Marrinan, J. A.; Frommer, B. R.; Thornton, R. A.; Mandala, S. M. J. Antibiot. 1992, 45, 1692-1696; Ikuina, Y.; Bando, C.; Yoshida, M.; Yano, H.; Saitoh, Y. J. Antibiot. 1997, 50, 998-1006; Becker, D.; Kiess, M.; Brückner, H. Liebigs Ann. Recueil 1997, 767-772.
2. For example: Walsh, J. J.; Metzler, D. E.; Powell, D.; Jacobson, R. A. J. Am. Chem. Soc. 1980, 102, 7136-7138; Kiick, D. M.; Cook, P. F. Biochemistry 1983, 22, 375-382; Saari, W. S.; Halczenko, W.; Cochran, D. W.; Dobrinska, M. R.; Vincek, W. C.; Titus, D. C.; Gaul, S. L.; Sweet, C. S. J. Med. Chem. 1984, 27, 713-717; Yamashita, T.; Iijima, M.; Nakamura, H.; Isshiki, K.; Naganawa, H.; Hattori, S.; Hamada, M.; Ishizuka, M.; Takeuchi, T. J. Antibiot. 1991, 44, 557-559; Horn, W. S.; Smith, J. L.; Bills, G. F.; Raghoobar, S. L.; Helms, G. L.; Kurtz, M. B.; Marrinan, J. A.; Frommer, B. R.; Thornton, R. A.; Mandala, S. M. J. Antibiot. 1992, 45, 1692-1696; Ikuina, Y.; Bando, C.; Yoshida, M.; Yano, H.; Saitoh, Y. J. Antibiot. 1997, 50, 998-1006; Becker, D.; Kiess, M.; Brückner, H. Liebigs Ann. Recueil 1997, 767-772.
3. For example: Walsh, J. J.; Metzler, D. E.; Powell, D.; Jacobson, R. A. J. Am. Chem. Soc. 1980, 102, 7136-7138; Kiick, D. M.; Cook, P. F. Biochemistry 1983, 22, 375-382; Saari, W. S.; Halczenko, W.; Cochran, D. W.; Dobrinska, M. R.; Vincek, W. C.; Titus, D. C.; Gaul, S. L.; Sweet, C. S. J. Med. Chem. 1984, 27, 713-717; Yamashita, T.; Iijima, M.; Nakamura, H.; Isshiki, K.; Naganawa, H.; Hattori, S.; Hamada, M.; Ishizuka, M.; Takeuchi, T. J. Antibiot. 1991, 44, 557-559; Horn, W. S.; Smith, J. L.; Bills, G. F.; Raghoobar, S. L.; Helms, G. L.; Kurtz, M. B.; Marrinan, J. A.; Frommer, B. R.; Thornton, R. A.; Mandala, S. M. J. Antibiot. 1992, 45, 1692-1696; Ikuina, Y.; Bando, C.; Yoshida, M.; Yano, H.; Saitoh, Y. J. Antibiot. 1997, 50, 998-1006; Becker, D.; Kiess, M.; Brückner, H. Liebigs Ann. Recueil 1997, 767-772.
4. For example: Walsh, J. J.; Metzler, D. E.; Powell, D.; Jacobson, R. A. J. Am. Chem. Soc. 1980, 102, 7136-7138; Kiick, D. M.; Cook, P. F. Biochemistry 1983, 22, 375-382; Saari, W. S.; Halczenko, W.; Cochran, D. W.; Dobrinska, M. R.; Vincek, W. C.; Titus, D. C.; Gaul, S. L.; Sweet, C. S. J. Med. Chem. 1984, 27, 713-717; Yamashita, T.; Iijima, M.; Nakamura, H.; Isshiki, K.; Naganawa, H.; Hattori, S.; Hamada, M.; Ishizuka, M.; Takeuchi, T. J. Antibiot. 1991, 44, 557-559; Horn, W. S.; Smith, J. L.; Bills, G. F.; Raghoobar, S. L.; Helms, G. L.; Kurtz, M. B.; Marrinan, J. A.; Frommer, B. R.; Thornton, R. A.; Mandala, S. M. J. Antibiot. 1992, 45, 1692-1696; Ikuina, Y.; Bando, C.; Yoshida, M.; Yano, H.; Saitoh, Y. J. Antibiot. 1997, 50, 998-1006; Becker, D.; Kiess, M.; Brückner, H. Liebigs Ann. Recueil 1997, 767-772.
5. For example: Walsh, J. J.; Metzler, D. E.; Powell, D.; Jacobson, R. A. J. Am. Chem. Soc. 1980, 102, 7136-7138; Kiick, D. M.; Cook, P. F. Biochemistry 1983, 22, 375-382; Saari, W. S.; Halczenko, W.; Cochran, D. W.; Dobrinska, M. R.; Vincek, W. C.; Titus, D. C.; Gaul, S. L.; Sweet, C. S. J. Med. Chem. 1984, 27, 713-717; Yamashita, T.; Iijima, M.; Nakamura, H.; Isshiki, K.; Naganawa, H.; Hattori, S.; Hamada, M.; Ishizuka, M.; Takeuchi, T. J. Antibiot. 1991, 44, 557-559; Horn, W. S.; Smith, J. L.; Bills, G. F.; Raghoobar, S. L.; Helms, G. L.; Kurtz, M. B.; Marrinan, J. A.; Frommer, B. R.; Thornton, R. A.; Mandala, S. M. J. Antibiot. 1992, 45, 1692-1696; Ikuina, Y.; Bando, C.; Yoshida, M.; Yano, H.; Saitoh, Y. J. Antibiot. 1997, 50, 998-1006; Becker, D.; Kiess, M.; Brückner, H. Liebigs Ann. Recueil 1997, 767-772.
6. For example: Walsh, J. J.; Metzler, D. E.; Powell, D.; Jacobson, R. A. J. Am. Chem. Soc. 1980, 102, 7136-7138; Kiick, D. M.; Cook, P. F. Biochemistry 1983, 22, 375-382; Saari, W. S.; Halczenko, W.; Cochran, D. W.; Dobrinska, M. R.; Vincek, W. C.; Titus, D. C.; Gaul, S. L.; Sweet, C. S. J. Med. Chem. 1984, 27, 713-717; Yamashita, T.; Iijima, M.; Nakamura, H.; Isshiki, K.; Naganawa, H.; Hattori, S.; Hamada, M.; Ishizuka, M.; Takeuchi, T. J. Antibiot. 1991, 44, 557-559; Horn, W. S.; Smith, J. L.; Bills, G. F.; Raghoobar, S. L.; Helms, G. L.; Kurtz, M. B.; Marrinan, J. A.; Frommer, B. R.; Thornton, R. A.; Mandala, S. M. J. Antibiot. 1992, 45, 1692-1696; Ikuina, Y.; Bando, C.; Yoshida, M.; Yano, H.; Saitoh, Y. J. Antibiot. 1997, 50, 998-1006; Becker, D.; Kiess, M.; Brückner, H. Liebigs Ann. Recueil 1997, 767-772.
7. For example: Walsh, J. J.; Metzler, D. E.; Powell, D.; Jacobson, R. A. J. Am. Chem. Soc. 1980, 102, 7136-7138; Kiick, D. M.; Cook, P. F. Biochemistry 1983, 22, 375-382; Saari, W. S.; Halczenko, W.; Cochran, D. W.; Dobrinska, M. R.; Vincek, W. C.; Titus, D. C.; Gaul, S. L.; Sweet, C. S. J. Med. Chem. 1984, 27, 713-717; Yamashita, T.; Iijima, M.; Nakamura, H.; Isshiki, K.; Naganawa, H.; Hattori, S.; Hamada, M.; Ishizuka, M.; Takeuchi, T. J. Antibiot. 1991, 44, 557-559; Horn, W. S.; Smith, J. L.; Bills, G. F.; Raghoobar, S. L.; Helms, G. L.; Kurtz, M. B.; Marrinan, J. A.; Frommer, B. R.; Thornton, R. A.; Mandala, S. M. J. Antibiot. 1992, 45, 1692-1696; Ikuina, Y.; Bando, C.; Yoshida, M.; Yano, H.; Saitoh, Y. J. Antibiot. 1997, 50, 998-1006; Becker, D.; Kiess, M.; Brückner, H. Liebigs Ann. Recueil 1997, 767-772.
8. For recent review: Cativiela, C.; Díaz-de-Villegas, M. D. Tetrahedron: Asymmetry 1998, 9, 3517-3599 and also see: Chinchilla, R.; Galindo, N.; Nájera, C. Synthesis 1999, 704-717.
9. For recent review: Cativiela, C.; Díaz-de-Villegas, M. D. Tetrahedron: Asymmetry 1998, 9, 3517-3599 and also see: Chinchilla, R.; Galindo, N.; Nájera, C. Synthesis 1999, 704-717.
10. Miyashita K., Miyabe H., Tai K., Kurozumi C., Iwaki H., Imanishi T. Tetrahedron. 55:1999;12109-12124.
11. (a) For pyridoxal model compounds with an ansa-structure, Ando, M; Kuzuhara, H. Bull. Chem. Soc. Jpn. 1990, 63, 1925-1928 and references cited therein.
12. (b) For those with a cyclodextrin-moiety and/or an amino side chain, Breslow, R.; Chmielewski, J.; Foley, D.; Johnson, B.; Kumabe, N.; Varney, M.; Mehra, R. Tetrahedron 1988, 44, 5515-5524 and references cited therein.
13. (c) For those with a functionalized bilayer vesicle, Kikuchi, J.; Zhang, Z.-Y.; Murakami, Y. J. Am. Chem. Soc. 1995, 117, 5383-5384 and references cited therein.
14. A part of this work appeared in a preliminary communication: Miyashita, K.; Miyabe, H.; Tai, K.; Kurozumi, C.; Imanishi, T. Chem. Commun. 1996, 1073-1074.
15. Kuzuhara H., Iwata M., Emoto S. J. Am. Chem. Soc. 99:1977;4173-4175.
16. 6 See also: Eliel, E. L. Stereochemistry of Carbon Compounds; McGraw-Hill: New York, 1962; p 175.
17. ansa-2A was recovered in 81% yield without loosing its optical purity.
18. Miyashita, K.; Miyabe, H.; Kurozumi, C.; Imanishi, T. Chem. Lett. 1995, 487-488; Miyashita, K.; Miyabe, H.; Kurozumi, C.; Tai, K.; Imanishi, T. Tetrahedron 1996, 52, 12125-12136.
19. Miyashita, K.; Miyabe, H.; Kurozumi, C.; Imanishi, T. Chem. Lett. 1995, 487-488; Miyashita, K.; Miyabe, H.; Kurozumi, C.; Tai, K.; Imanishi, T. Tetrahedron 1996, 52, 12125-12136.
20. Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; Wiley: New York, 1995; pp 36-41; Tolbert, L. M., Ali, M. B. J. Am. Chem. Soc. 1984, 106, 3806-3810.
21. Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; Wiley: New York, 1995; pp 36-41; Tolbert, L. M., Ali, M. B. J. Am. Chem. Soc. 1984, 106, 3806-3810.
22. A similar hypothesis was proposed by Kuzuhara and coworkers as well: Kuzuhara, H.; Watanabe, N.; Ando, M. J. Chem. Soc., Chem. Commun. 1987, 95-96.
23. +: Olsher, U.; Izatt, R. M.; Bradshaw, J. S.; Dalley, N. K. Chem. Rev. 1991, 91, 137-164.
24. ansa-12 might also explain the diastereoface selective alkylation from the ansa-chain as shown in Fig. 4
25. ansa-2A is illustrated in Fig. 3 in order to clarify the effect of double asymmetric induction.
26. Asymmetric catalysts bearing a combination of a central chirality and an axial chirality have been already reported, but the double asymmetric induction effect is ambiguous. For example: Sasaki, H.; Irie, R.; Hamada, T.; Suzuki, K.; Katsuki, T. Tetrahedron 1994, 50, 11827-11838; Ito, Y. N.; Katsuki, T. Bull. Chem. Soc. Jpn. 1999, 72, 603-619; Ducry, L.; Diederich, F. Helv. Chim. Acta 1999, 82, 981-1004.
27. Asymmetric catalysts bearing a combination of a central chirality and an axial chirality have been already reported, but the double asymmetric induction effect is ambiguous. For example: Sasaki, H.; Irie, R.; Hamada, T.; Suzuki, K.; Katsuki, T. Tetrahedron 1994, 50, 11827-11838; Ito, Y. N.; Katsuki, T. Bull. Chem. Soc. Jpn. 1999, 72, 603-619; Ducry, L.; Diederich, F. Helv. Chim. Acta 1999, 82, 981-1004.
28. Asymmetric catalysts bearing a combination of a central chirality and an axial chirality have been already reported, but the double asymmetric induction effect is ambiguous. For example: Sasaki, H.; Irie, R.; Hamada, T.; Suzuki, K.; Katsuki, T. Tetrahedron 1994, 50, 11827-11838; Ito, Y. N.; Katsuki, T. Bull. Chem. Soc. Jpn. 1999, 72, 603-619; Ducry, L.; Diederich, F. Helv. Chim. Acta 1999, 82, 981-1004.