Catalytic asymmetric synthesis of α-amino acid derivatives and peptides using chiral phase-transfer catalysts

Proceedings of the Japan Academy Series B: Physical and Biological Sciences

Volumn 79, Issue 7, 2003, Pages 181-189

  Maruoka, Keiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Aldol; Asymmetric alkylation; Phase transfer catalyst; tert butyl glycinate; amino acid

Indexed keywords

EID: 0346338137     PISSN: 03862208     EISSN: None     Source Type: Journal    
DOI: 10.2183/pjab.79B.181     Document Type: Review

References (35)

1. For representative reviews on the preparation of optically active α-amino acids, see: (a) Williams, R. M. (1989) In Synthesis of Optically Active α-Amino Acids (ed. Baldwin, J. E.). Organic Chemistry Series. Pergamon Press, Oxford. (b) Williams, R. M., and Hendrix, J A. (1992) Chem. Rev. 92, 889-917. (c) Duthaler, R. O. (1994) Tetrahedron 50, 1539-1650. (d) Seebach, D., Sting, A R., and Hoffmann, M. (1996) Angew. Chem Int Ed. Engl. 35, 2708-2748. (e) Cativiela, C , and Díaz-de-Villegas, M. D. (1998) Tetrahedron: Asymmetry 9, 3517-3599.
2. For representative reviews on the preparation of optically active α-amino acids, see: (a) Williams, R. M. (1989) In Synthesis of Optically Active α-Amino Acids (ed. Baldwin, J. E.). Organic Chemistry Series. Pergamon Press, Oxford. (b) Williams, R. M., and Hendrix, J A. (1992) Chem. Rev. 92, 889-917. (c) Duthaler, R. O. (1994) Tetrahedron 50, 1539-1650. (d) Seebach, D., Sting, A R., and Hoffmann, M. (1996) Angew. Chem Int Ed. Engl. 35, 2708-2748. (e) Cativiela, C , and Díaz-de-Villegas, M. D. (1998) Tetrahedron: Asymmetry 9, 3517-3599.
3. For representative reviews on the preparation of optically active α-amino acids, see: (a) Williams, R. M. (1989) In Synthesis of Optically Active α-Amino Acids (ed. Baldwin, J. E.). Organic Chemistry Series. Pergamon Press, Oxford. (b) Williams, R. M., and Hendrix, J A. (1992) Chem. Rev. 92, 889-917. (c) Duthaler, R. O. (1994) Tetrahedron 50, 1539-1650. (d) Seebach, D., Sting, A R., and Hoffmann, M. (1996) Angew. Chem Int Ed. Engl. 35, 2708-2748. (e) Cativiela, C , and Díaz-de-Villegas, M. D. (1998) Tetrahedron: Asymmetry 9, 3517-3599.
4. For representative reviews on the preparation of optically active α-amino acids, see: (a) Williams, R. M. (1989) In Synthesis of Optically Active α-Amino Acids (ed. Baldwin, J. E.). Organic Chemistry Series. Pergamon Press, Oxford. (b) Williams, R. M., and Hendrix, J A. (1992) Chem. Rev. 92, 889-917. (c) Duthaler, R. O. (1994) Tetrahedron 50, 1539-1650. (d) Seebach, D., Sting, A R., and Hoffmann, M. (1996) Angew. Chem Int Ed. Engl. 35, 2708-2748. (e) Cativiela, C , and Díaz-de-Villegas, M. D. (1998) Tetrahedron: Asymmetry 9, 3517-3599.
5. For representative reviews on the preparation of optically active α-amino acids, see: (a) Williams, R. M. (1989) In Synthesis of Optically Active α-Amino Acids (ed. Baldwin, J. E.). Organic Chemistry Series. Pergamon Press, Oxford. (b) Williams, R. M., and Hendrix, J A. (1992) Chem. Rev. 92, 889-917. (c) Duthaler, R. O. (1994) Tetrahedron 50, 1539-1650. (d) Seebach, D., Sting, A R., and Hoffmann, M. (1996) Angew. Chem Int Ed. Engl. 35, 2708-2748. (e) Cativiela, C , and Díaz-de-Villegas, M. D. (1998) Tetrahedron: Asymmetry 9, 3517-3599.
6. Recent reviews on phase-transfer reactions: (a) Dehmlow, E. V., and Dehmlow, S. S. (1993) Phase Transfer Catalysis. 3rd ed., VCH, Weinheim. (b) Starks, C. M., Liotta. C. L., and Halpern, M. (1994) Phase-Transfer Catalysis. Chapman & Hall, New York. (c) Sasson, Y., and Neumann, R (eds.) (1997) Handbook of Phase-Transfer Catalysis. Blackie Academic & Professional, London. (d) Halpern, M E. (ed.) (1997) Phase-Transfer Catalysis. ACS Symposium Series. Vol. 659, American Chemical Society, Washington, DC
7. Recent reviews on phase-transfer reactions: (a) Dehmlow, E. V., and Dehmlow, S. S. (1993) Phase Transfer Catalysis. 3rd ed., VCH, Weinheim. (b) Starks, C. M., Liotta. C. L., and Halpern, M. (1994) Phase-Transfer Catalysis. Chapman & Hall, New York. (c) Sasson, Y., and Neumann, R (eds.) (1997) Handbook of Phase-Transfer Catalysis. Blackie Academic & Professional, London. (d) Halpern, M E. (ed.) (1997) Phase-Transfer Catalysis. ACS Symposium Series. Vol. 659, American Chemical Society, Washington, DC
8. Recent reviews on phase-transfer reactions: (a) Dehmlow, E. V., and Dehmlow, S. S. (1993) Phase Transfer Catalysis. 3rd ed., VCH, Weinheim. (b) Starks, C. M., Liotta, C. L., and Halpern, M. (1994) Phase-Transfer Catalysis. Chapman & Hall, New York. (c) Sasson, Y., and Neumann, R (eds.) (1997) Handbook of Phase-Transfer Catalysis. Blackie Academic & Professional, London. (d) Halpern, M E. (ed.) (1997) Phase-Transfer Catalysis. ACS Symposium Series. Vol. 659, American Chemical Society, Washington, DC
9. Recent reviews on phase-transfer reactions: (a) Dehmlow, E. V., and Dehmlow, S. S. (1993) Phase Transfer Catalysis. 3rd ed., VCH, Weinheim. (b) Starks, C. M., Liotta, C. L., and Halpern, M. (1994) Phase-Transfer Catalysis. Chapman & Hall, New York. (c) Sasson, Y., and Neumann, R (eds.) (1997) Handbook of Phase-Transfer Catalysis. Blackie Academic & Professional, London. (d) Halpern, M E. (ed.) (1997) Phase-Transfer Catalysis. ACS Symposium Series. Vol. 659, American Chemical Society, Washington, DC
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