Enantioselective alkylation of alanine-derived imines using quaternary ammonium catalysts.

Tetrahedron Letters

Volumn 40, Issue 49, 1999, Pages 8671-8674

  Lygo, Barry ^a   Crosby, John ^b   Peterson, Justine A ^a  

^a UNIVERSITY OF SALFORD   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALANINE DERIVATIVE; ALPHA AMINO ACID; IMINE; QUATERNARY AMMONIUM DERIVATIVE;

ALKYLATION; ARTICLE; CATALYST; ENANTIOMER; MOLECULAR INTERACTION; STEREOISOMERISM; SYNTHESIS;

EID: 0033520975     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01836-5     Document Type: Article

References (35)

1. Current Address: School of Chemistry, Nottingham University, Nottingham, NG7 2RD, UK
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3. For recent reviews relating to the synthesis of chiral α,α-dialkyl-α-amino acids see: Cativiela, C; Diaz-de-Villegas, M.D. Tetrahedron Asymm., 1998, 9, 3517; Williams, R.M. "Synthesis of Opticallyactive α-Amino Acids", Pergamon Press, Oxford, 1989; Wirth, T. Angew. Chem. Int. Ed. Engl., 1997, 36, 225; Seebach, D; Sting, A.R; Hoffmann, M. Angew. Chem. Int. Ed. Engl., 1996, 35, 2708.
4. For recent reviews relating to the synthesis of chiral α,α-dialkyl-α-amino acids see: Cativiela, C; Diaz-de-Villegas, M.D. Tetrahedron Asymm., 1998, 9, 3517; Williams, R.M. "Synthesis of Opticallyactive α-Amino Acids", Pergamon Press, Oxford, 1989; Wirth, T. Angew. Chem. Int. Ed. Engl., 1997, 36, 225; Seebach, D; Sting, A.R; Hoffmann, M. Angew. Chem. Int. Ed. Engl., 1996, 35, 2708.
5. See for example: Vedejs, E; Fields, S.C; Hayashi, R; Hitchcock, S.R; Powell, D.R; Schrimpf, M.R. J. Am. Chem. Soc., 1999, 121, 2460; Belokon, Y.N; Kochetkov, K.A; Churkina, T.D; Ikonnikov, N.S; Chesnokov, A.A; Larionov, O.V; Parmár, V.S; Kumar, R; Kagan, H.B. Tetrahedron Asymm., 1998, 9, 851; Belokon, Y.N; North, M; Kublitski, V.S; Ikonnikov, N.S; Krasik, P.E; Maleev, V.I. Tetrahedron Lett., 1999, 40, 6105; and references therein.
6. See for example: Vedejs, E; Fields, S.C; Hayashi, R; Hitchcock, S.R; Powell, D.R; Schrimpf, M.R. J. Am. Chem. Soc., 1999, 121, 2460; Belokon, Y.N; Kochetkov, K.A; Churkina, T.D; Ikonnikov, N.S; Chesnokov, A.A; Larionov, O.V; Parmár, V.S; Kumar, R; Kagan, H.B. Tetrahedron Asymm., 1998, 9, 851; Belokon, Y.N; North, M; Kublitski, V.S; Ikonnikov, N.S; Krasik, P.E; Maleev, V.I. Tetrahedron Lett., 1999, 40, 6105; and references therein.
7. See for example: Vedejs, E; Fields, S.C; Hayashi, R; Hitchcock, S.R; Powell, D.R; Schrimpf, M.R. J. Am. Chem. Soc., 1999, 121, 2460; Belokon, Y.N; Kochetkov, K.A; Churkina, T.D; Ikonnikov, N.S; Chesnokov, A.A; Larionov, O.V; Parmár, V.S; Kumar, R; Kagan, H.B. Tetrahedron Asymm., 1998, 9, 851; Belokon, Y.N; North, M; Kublitski, V.S; Ikonnikov, N.S; Krasik, P.E; Maleev, V.I. Tetrahedron Lett., 1999, 40, 6105; and references therein.
8. See for example: Vedejs, E; Fields, S.C; Hayashi, R; Hitchcock, S.R; Powell, D.R; Schrimpf, M.R. J. Am. Chem. Soc., 1999, 121, 2460; Belokon, Y.N; Kochetkov, K.A; Churkina, T.D; Ikonnikov, N.S; Chesnokov, A.A; Larionov, O.V; Parmár, V.S; Kumar, R; Kagan, H.B. Tetrahedron Asymm., 1998, 9, 851; Belokon, Y.N; North, M; Kublitski, V.S; Ikonnikov, N.S; Krasik, P.E; Maleev, V.I. Tetrahedron Lett., 1999, 40, 6105; and references therein.
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12. For the application of N-anthracenylmethyl substituted Cinchona alkaloids to the asymmetric alkylation of glycine imines see: Lygo, B; Wainwright, P.G. Tetrahedron Lett., 1997, 38, 8595; Lygo, B; Crosby J; Peterson, J.A. Tetrahedron Lett., 1999, 40, 1385; Lygo, B. Tetrahedron Lett., 1999, 40, 1389.
13. For the application of N-anthracenylmethyl substituted Cinchona alkaloids to the asymmetric alkylation of glycine imines see: Lygo, B; Wainwright, P.G. Tetrahedron Lett., 1997, 38, 8595; Lygo, B; Crosby J; Peterson, J.A. Tetrahedron Lett., 1999, 40, 1385; Lygo, B. Tetrahedron Lett., 1999, 40, 1389.
14. For the application of N-anthracenylmethyl substituted Cinchona alkaloids to the asymmetric alkylation of glycine imines see: Lygo, B; Wainwright, P.G. Tetrahedron Lett., 1997, 38, 8595; Lygo, B; Crosby J; Peterson, J.A. Tetrahedron Lett., 1999, 40, 1385; Lygo, B. Tetrahedron Lett., 1999, 40, 1389.
15. For the application of N-anthracenylmethyl substituted Cinchona alkaloids to the asymmetric epoxidation of enones see: Lygo, B; Wainwright, P.G. Tetrahedron Lett., 1998, 39, 1599; Lygo, B; Wainwright, P.G. Tetrahedron, 1999, 55, 6289.
16. For the application of N-anthracenylmethyl substituted Cinchona alkaloids to the asymmetric epoxidation of enones see: Lygo, B; Wainwright, P.G. Tetrahedron Lett., 1998, 39, 1599; Lygo, B; Wainwright, P.G. Tetrahedron, 1999, 55, 6289.
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23. For earlier work on the enantioselective alkylation of glycine imines under liquid-liquid phase-transfer conditions see: Esikova, I.A; Nahreini, T.S; O'Donnell, M.J. in ®ACS Symposium Series 659: Phase-transfer Catalysis - Mechanisms and Syntheses", Ed. Halpern, M.E., ACS, Washington D.C, 1997, p89; O'Donnell, M.J; Esikova, I.A; Mi, A; Shullenberger, D.F; Wu, S. in "ACS Symposium Series 659: Phase-transfer Catalysis - Mechanisms and Syntheses", Ed. Halpern, M.E., ACS, Washington D.C,1997, p124; O'Donnell, M.J; Wu, S; Esikova, I; Mi, A. U.S. Patent 5,554,753, September 10, 1996; O'Donnell, M.J; Wu, S; Huffman, J.C. Tetrahderon, 1994, 50, 4507; Tohdo, K; Hamada, Y; Shioiri, T. Synlett, 1994, 247; Imperiali, B; Fisher, S.L. J. Org. Chem., 1992, 57, 757; Tohdo, K; Hamada, Y; Shioiri, T. Pept. Chem., 1991, 7; O'Donnell, M.J; Bennett, W.D; Wu, S. J. Am. Chem. Soc.,1989, 111, 2353.
24. For earlier work on the enantioselective alkylation of glycine imines under liquid-liquid phase-transfer conditions see: Esikova, I.A; Nahreini, T.S; O'Donnell, M.J. in ®ACS Symposium Series 659: Phase-transfer Catalysis - Mechanisms and Syntheses", Ed. Halpern, M.E., ACS, Washington D.C, 1997, p89; O'Donnell, M.J; Esikova, I.A; Mi, A; Shullenberger, D.F; Wu, S. in "ACS Symposium Series 659: Phase-transfer Catalysis - Mechanisms and Syntheses", Ed. Halpern, M.E., ACS, Washington D.C,1997, p124; O'Donnell, M.J; Wu, S; Esikova, I; Mi, A. U.S. Patent 5,554,753, September 10, 1996; O'Donnell, M.J; Wu, S; Huffman, J.C. Tetrahderon, 1994, 50, 4507; Tohdo, K; Hamada, Y; Shioiri, T. Synlett, 1994, 247; Imperiali, B; Fisher, S.L. J. Org. Chem., 1992, 57, 757; Tohdo, K; Hamada, Y; Shioiri, T. Pept. Chem., 1991, 7; O'Donnell, M.J; Bennett, W.D; Wu, S. J. Am. Chem. Soc.,1989, 111, 2353.
25. For earlier work on the enantioselective alkylation of glycine imines under liquid-liquid phase-transfer conditions see: Esikova, I.A; Nahreini, T.S; O'Donnell, M.J. in ®ACS Symposium Series 659: Phase-transfer Catalysis - Mechanisms and Syntheses", Ed. Halpern, M.E., ACS, Washington D.C, 1997, p89; O'Donnell, M.J; Esikova, I.A; Mi, A; Shullenberger, D.F; Wu, S. in "ACS Symposium Series 659: Phase-transfer Catalysis - Mechanisms and Syntheses", Ed. Halpern, M.E., ACS, Washington D.C,1997, p124; O'Donnell, M.J; Wu, S; Esikova, I; Mi, A. U.S. Patent 5,554,753, September 10, 1996; O'Donnell, M.J; Wu, S; Huffman, J.C. Tetrahderon, 1994, 50, 4507; Tohdo, K; Hamada, Y; Shioiri, T. Synlett, 1994, 247; Imperiali, B; Fisher, S.L. J. Org. Chem., 1992, 57, 757; Tohdo, K; Hamada, Y; Shioiri, T. Pept. Chem., 1991, 7; O'Donnell, M.J; Bennett, W.D; Wu, S. J. Am. Chem. Soc.,1989, 111, 2353.
26. For earlier work on the enantioselective alkylation of glycine imines under liquid-liquid phase-transfer conditions see: Esikova, I.A; Nahreini, T.S; O'Donnell, M.J. in ®ACS Symposium Series 659: Phase-transfer Catalysis - Mechanisms and Syntheses", Ed. Halpern, M.E., ACS, Washington D.C, 1997, p89; O'Donnell, M.J; Esikova, I.A; Mi, A; Shullenberger, D.F; Wu, S. in "ACS Symposium Series 659: Phase-transfer Catalysis - Mechanisms and Syntheses", Ed. Halpern, M.E., ACS, Washington D.C,1997, p124; O'Donnell, M.J; Wu, S; Esikova, I; Mi, A. U.S. Patent 5,554,753, September 10, 1996; O'Donnell, M.J; Wu, S; Huffman, J.C. Tetrahderon, 1994, 50, 4507; Tohdo, K; Hamada, Y; Shioiri, T. Synlett, 1994, 247; Imperiali, B; Fisher, S.L. J. Org. Chem., 1992, 57, 757; Tohdo, K; Hamada, Y; Shioiri, T. Pept. Chem., 1991, 7; O'Donnell, M.J; Bennett, W.D; Wu, S. J. Am. Chem. Soc.,1989, 111, 2353.
27. For earlier work on the enantioselective alkylation of glycine imines under liquid-liquid phase-transfer conditions see: Esikova, I.A; Nahreini, T.S; O'Donnell, M.J. in ®ACS Symposium Series 659: Phase-transfer Catalysis - Mechanisms and Syntheses", Ed. Halpern, M.E., ACS, Washington D.C, 1997, p89; O'Donnell, M.J; Esikova, I.A; Mi, A; Shullenberger, D.F; Wu, S. in "ACS Symposium Series 659: Phase-transfer Catalysis - Mechanisms and Syntheses", Ed. Halpern, M.E., ACS, Washington D.C,1997, p124; O'Donnell, M.J; Wu, S; Esikova, I; Mi, A. U.S. Patent 5,554,753, September 10, 1996; O'Donnell, M.J; Wu, S; Huffman, J.C. Tetrahderon, 1994, 50, 4507; Tohdo, K; Hamada, Y; Shioiri, T. Synlett, 1994, 247; Imperiali, B; Fisher, S.L. J. Org. Chem., 1992, 57, 757; Tohdo, K; Hamada, Y; Shioiri, T. Pept. Chem., 1991, 7; O'Donnell, M.J; Bennett, W.D; Wu, S. J. Am. Chem. Soc.,1989, 111, 2353.
28. For earlier work on the enantioselective alkylation of glycine imines under liquid-liquid phase-transfer conditions see: Esikova, I.A; Nahreini, T.S; O'Donnell, M.J. in ®ACS Symposium Series 659: Phase-transfer Catalysis - Mechanisms and Syntheses", Ed. Halpern, M.E., ACS, Washington D.C, 1997, p89; O'Donnell, M.J; Esikova, I.A; Mi, A; Shullenberger, D.F; Wu, S. in "ACS Symposium Series 659: Phase-transfer Catalysis - Mechanisms and Syntheses", Ed. Halpern, M.E., ACS, Washington D.C,1997, p124; O'Donnell, M.J; Wu, S; Esikova, I; Mi, A. U.S. Patent 5,554,753, September 10, 1996; O'Donnell, M.J; Wu, S; Huffman, J.C. Tetrahderon, 1994, 50, 4507; Tohdo, K; Hamada, Y; Shioiri, T. Synlett, 1994, 247; Imperiali, B; Fisher, S.L. J. Org. Chem., 1992, 57, 757; Tohdo, K; Hamada, Y; Shioiri, T. Pept. Chem., 1991, 7; O'Donnell, M.J; Bennett, W.D; Wu, S. J. Am. Chem. Soc.,1989, 111, 2353.
29. For earlier work on the enantioselective alkylation of glycine imines under liquid-liquid phase-transfer conditions see: Esikova, I.A; Nahreini, T.S; O'Donnell, M.J. in ®ACS Symposium Series 659: Phase-transfer Catalysis - Mechanisms and Syntheses", Ed. Halpern, M.E., ACS, Washington D.C, 1997, p89; O'Donnell, M.J; Esikova, I.A; Mi, A; Shullenberger, D.F; Wu, S. in "ACS Symposium Series 659: Phase-transfer Catalysis - Mechanisms and Syntheses", Ed. Halpern, M.E., ACS, Washington D.C,1997, p124; O'Donnell, M.J; Wu, S; Esikova, I; Mi, A. U.S. Patent 5,554,753, September 10, 1996; O'Donnell, M.J; Wu, S; Huffman, J.C. Tetrahderon, 1994, 50, 4507; Tohdo, K; Hamada, Y; Shioiri, T. Synlett, 1994, 247; Imperiali, B; Fisher, S.L. J. Org. Chem., 1992, 57, 757; Tohdo, K; Hamada, Y; Shioiri, T. Pept. Chem., 1991, 7; O'Donnell, M.J; Bennett, W.D; Wu, S. J. Am. Chem. Soc.,1989, 111, 2353.
30. For earlier work on the enantioselective alkylation of glycine imines under liquid-liquid phase-transfer conditions see: Esikova, I.A; Nahreini, T.S; O'Donnell, M.J. in ®ACS Symposium Series 659: Phase-transfer Catalysis - Mechanisms and Syntheses", Ed. Halpern, M.E., ACS, Washington D.C, 1997, p89; O'Donnell, M.J; Esikova, I.A; Mi, A; Shullenberger, D.F; Wu, S. in "ACS Symposium Series 659: Phase-transfer Catalysis - Mechanisms and Syntheses", Ed. Halpern, M.E., ACS, Washington D.C,1997, p124; O'Donnell, M.J; Wu, S; Esikova, I; Mi, A. U.S. Patent 5,554,753, September 10, 1996; O'Donnell, M.J; Wu, S; Huffman, J.C. Tetrahderon, 1994, 50, 4507; Tohdo, K; Hamada, Y; Shioiri, T. Synlett, 1994, 247; Imperiali, B; Fisher, S.L. J. Org. Chem., 1992, 57, 757; Tohdo, K; Hamada, Y; Shioiri, T. Pept. Chem., 1991, 7; O'Donnell, M.J; Bennett, W.D; Wu, S. J. Am. Chem. Soc.,1989, 111, 2353.
31. It is important to note that the catalyst structure is modified by rapid O-alkylation under the reaction conditions, however generally the nature of the alkylating group has little influence on the enantioselectivity of the resulting reaction processes.
32. 4) and concentrated under reduced pressure to give the crude amino acid esters which could be purified by chromatography on silica gel (ethyl acetate) or by crystallisation.
33. 2) followed by HPLC analysis (Chiralcel OD-H, i-propanol/hexane, 254nm). In all cases the stereochemically enriched samples were compared with statistical mixtures generated using tetra-butylammonium bromide as the catalyst for alkylation.
34. The absolute stereochemistry of this material was determined by cleavage of the tert-butyl ester (6M HCl), and comparison of the rotation of the free amino acid with known data (Cativiela, C; Diaz-de-Villegas, M.D; Galvez, J.A. Tetrahedron Asymm., 1994, 5, 261).
35. For example the N-benzoyl derivative of (S)-α-methylphenylalanine 5 (87% e.e.) can be obtained in ≥97% e.e. by a single crystallisation from ethyl acetate / petroleum ether (72% recovery).