Catalytic, asymmetric synthesis of α,α-disubstituted amino acids

Tetrahedron Letters

Volumn 44, Issue 10, 2003, Pages 2045-2048

  Belokon', Yuri N ^b   Bhave, Devayani ^a   D'Addario, Daniela ^a   Groaz, Elizabetta ^a   Maleev, Viktor ^b   North, Michael ^a   Pertrosyan, Armine ^b  

^a KING'S COLLEGE LONDON   (United Kingdom)

^b A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

Author keywords

Asymmetric catalysis; Copper(salen) complex; Enolate alkylation; , disubstituted amino acid

Indexed keywords

4 AMINOBUTYRIC ACID; ALANINE; ALLYLGLYCINE; AMINO ACID DERIVATIVE; COPPER COMPLEX; LEUCINE; PHENYLALANINE; VALINE;

ALKYLATION; ARTICLE; CATALYST; ENANTIOSELECTIVITY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0037416926     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00170-9     Document Type: Article

References (23)

1. See for example: (a) 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. l984, 27, 713; (b) Fenteany, G.; Standeart, R. F.; Lane, W. S.; Choi, S.; Corey, E. J.; Schreiber, S. L. Science 1995, 268, 726; (c) Hanessian, S.; Haskell, T. H. Tetrahedron Lett. 1964, 2451; (d) Jung, G.; Beck-Sickinger, A. G. Angew. Chem., Int. Ed. Engl. 1992, 31, 367; (e) Veber, D. F.; Freidinger, R. M. Trends Neuorosci. 1995, 8, 392.
2. See for example: (a) 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. l984, 27, 713; (b) Fenteany, G.; Standeart, R. F.; Lane, W. S.; Choi, S.; Corey, E. J.; Schreiber, S. L. Science 1995, 268, 726; (c) Hanessian, S.; Haskell, T. H. Tetrahedron Lett. 1964, 2451; (d) Jung, G.; Beck-Sickinger, A. G. Angew. Chem., Int. Ed. Engl. 1992, 31, 367; (e) Veber, D. F.; Freidinger, R. M. Trends Neuorosci. 1995, 8, 392.
3. See for example: (a) 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. l984, 27, 713; (b) Fenteany, G.; Standeart, R. F.; Lane, W. S.; Choi, S.; Corey, E. J.; Schreiber, S. L. Science 1995, 268, 726; (c) Hanessian, S.; Haskell, T. H. Tetrahedron Lett. 1964, 2451; (d) Jung, G.; Beck-Sickinger, A. G. Angew. Chem., Int. Ed. Engl. 1992, 31, 367; (e) Veber, D. F.; Freidinger, R. M. Trends Neuorosci. 1995, 8, 392.
4. See for example: (a) 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. l984, 27, 713; (b) Fenteany, G.; Standeart, R. F.; Lane, W. S.; Choi, S.; Corey, E. J.; Schreiber, S. L. Science 1995, 268, 726; (c) Hanessian, S.; Haskell, T. H. Tetrahedron Lett. 1964, 2451; (d) Jung, G.; Beck-Sickinger, A. G. Angew. Chem., Int. Ed. Engl. 1992, 31, 367; (e) Veber, D. F.; Freidinger, R. M. Trends Neuorosci. 1995, 8, 392.
5. See for example: (a) 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. l984, 27, 713; (b) Fenteany, G.; Standeart, R. F.; Lane, W. S.; Choi, S.; Corey, E. J.; Schreiber, S. L. Science 1995, 268, 726; (c) Hanessian, S.; Haskell, T. H. Tetrahedron Lett. 1964, 2451; (d) Jung, G.; Beck-Sickinger, A. G. Angew. Chem., Int. Ed. Engl. 1992, 31, 367; (e) Veber, D. F.; Freidinger, R. M. Trends Neuorosci. 1995, 8, 392.
6. For a leading reference, see: Toniolo C., Crisma M., Formaggio F., Peggion C. Biopolymers. 60:2001;396-419.
7. Schollkopf U., Tolle R., Egert E., Nieger M. Liebigs Ann. Chem. 1987;399-405.
8. Yamada S.-I., Oguri T., Shioiri T. J. Chem. Soc., Chem. Commun. 1976;136-137.
9. Ikegami S., Uchiyama H., Hayama T., Katsuki T., Yamaguchi M. Tetrahedron. 44:1988;5333-5342.
10. Belokon Y.N., North M., Kublitski V.S., Ikonnikov N.S., Krasik P.E., Maleev V.I. Tetrahedron Lett. 40:1999;6105-6108.
11. Belokon Y.N., North M., Churkina T.D., Ikonnikov N.S., Maleev V.I. Tetrahedron. 57:2001;2491-2498.
12. Belokon' Y.N., Davies R.G., North M. Tetrahedron Lett. 41:2000;7245-7248.
13. Belokon' Y.N., Davies R.G., Fuentes J.A., North M., Parsons T. Tetrahedron Lett. 42:2001;8093-8096.
14. Lygo B., Crosby J., Peterson J.A. Tetrahedron Lett. 40:1999;8671-8674.
15. Ooi T., Kameda M., Maruoka K. J. Am. Chem. Soc. 121:1999;6519-6520.
16. Ooi T., Takeuchi M., Kameda M., Maruoka K. J. Am. Chem. Soc. 122:2000;5228-5229.
17. Ooi T., Takeuchi M., Ohara D., Maruoka K. Synlett. 2001;1185-1187.
18. Belokon' Y.N., Kochetkov K.A., Churkina T.D., Ikonnikov N.S., Chesnokov A.A., Larionov O.V., Parmar V.S., Kumar R., Kagan H.B. Tetrahedron: Asymmetry. 9:1998;851-857.
19. Belokon' Y.N., Kochetkov K.A., Churkina T.D., Ikonnikov N.S., Vyskocil S., Kagan H.B. Tetrahedron: Asymmetry. 10:1999;1723-1728.
20. All new compounds gave satisfactory spectroscopic data.
21. Kingma I.E., Wiersma M., van der Baan J.L., Balt S., Bickelhaupt F., de Bolster M.W.G., Klumpp G.W., Spek A.L. J. Chem. Soc., Chem. Commun. 1993;832-834.
22. Blaauw R., Kingma I.E., Laan J.H., van der Baan J.L., Balt S., de Bolster M.W.G., Klumpp G.W., Smeets W.J.J., Spek A.L. J. Chem. Soc., Perkin Trans. 1. 2000;1199-1210.
23. Vedejs E., Fields S.C., Hayashi R., Hitchcock S.R., Powell D.R., Schrimpf M.R. J. Am. Chem. Soc. 121:1999;2460-2470.