Convenient, asymmetric synthesis of enantiomerically pure 2',6'- dimethyltyrosine (DMT) via alkylation of chiral equivalent of nucleophilic glycine

Tetrahedron Asymmetry

Volumn 11, Issue 14, 2000, Pages 2917-2925

  Tang, Xuejun ^a   Soloshonok, Vadim A ^a   Hruby, Victor J ^a  

^a University of Arizona   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOPHENONE DERIVATIVE; BENZYL DERIVATIVE; BROMINE DERIVATIVE; GLYCINE; NICKEL COMPLEX; TYROSINE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHIRALITY; DIASTEREOISOMER; ENANTIOMER; HYDROGENATION; PRIORITY JOURNAL; STEREOSPECIFICITY; SYNTHESIS; TEMPERATURE DEPENDENCE;

EID: 0034725677     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00250-0     Document Type: Article

References (33)

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16. For reviews on reactivity, properties and applications of complex (S)-1 in the asymmetric synthesis of α-amino acids, see: (a) Belokon, Yu. N. Janssen Chimica Acta 1992, 10, 4. (b) Belokon, Yu. N. Pure Appl. Chem. 1992, 64, 1917. (c) Kukhar', V. P.; Resnati, G.; Soloshonok, V. A. In Fluorine-Containing Amino Acids. Synthesis and Properties; Kukhar', V. P.; Soloshonok, V. A., Eds.; John Wiley & Sons: Chichester, 1994; Chapter 5. (d) Soloshonok, V. A. In Biomedical Frontiers of Fluorine Chemistry; Ojima, I.; McCarthy, J. R.; Welch, J. T., Eds.; ACS Books, American Chemical Society: Washington, DC, 1996; Chapter 2. (e) Soloshonok, V. A. In Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedicinal Targets; Soloshonok, V. A. Ed.; John Wiley & Sons: Chichester, 1999; Chapter 7.
17. For reviews on reactivity, properties and applications of complex (S)-1 in the asymmetric synthesis of α-amino acids, see: (a) Belokon, Yu. N. Janssen Chimica Acta 1992, 10, 4. (b) Belokon, Yu. N. Pure Appl. Chem. 1992, 64, 1917. (c) Kukhar', V. P.; Resnati, G.; Soloshonok, V. A. In Fluorine-Containing Amino Acids. Synthesis and Properties; Kukhar', V. P.; Soloshonok, V. A., Eds.; John Wiley & Sons: Chichester, 1994; Chapter 5. (d) Soloshonok, V. A. In Biomedical Frontiers of Fluorine Chemistry; Ojima, I.; McCarthy, J. R.; Welch, J. T., Eds.; ACS Books, American Chemical Society: Washington, DC, 1996; Chapter 2. (e) Soloshonok, V. A. In Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedicinal Targets; Soloshonok, V. A. Ed.; John Wiley & Sons: Chichester, 1999; Chapter 7.
18. For reviews on reactivity, properties and applications of complex (S)-1 in the asymmetric synthesis of α-amino acids, see: (a) Belokon, Yu. N. Janssen Chimica Acta 1992, 10, 4. (b) Belokon, Yu. N. Pure Appl. Chem. 1992, 64, 1917. (c) Kukhar', V. P.; Resnati, G.; Soloshonok, V. A. In Fluorine-Containing Amino Acids. Synthesis and Properties; Kukhar', V. P.; Soloshonok, V. A., Eds.; John Wiley & Sons: Chichester, 1994; Chapter 5. (d) Soloshonok, V. A. In Biomedical Frontiers of Fluorine Chemistry; Ojima, I.; McCarthy, J. R.; Welch, J. T., Eds.; ACS Books, American Chemical Society: Washington, DC, 1996; Chapter 2. (e) Soloshonok, V. A. In Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedicinal Targets; Soloshonok, V. A. Ed.; John Wiley & Sons: Chichester, 1999; Chapter 7.
19. For reviews on reactivity, properties and applications of complex (S)-1 in the asymmetric synthesis of α-amino acids, see: (a) Belokon, Yu. N. Janssen Chimica Acta 1992, 10, 4. (b) Belokon, Yu. N. Pure Appl. Chem. 1992, 64, 1917. (c) Kukhar', V. P.; Resnati, G.; Soloshonok, V. A. In Fluorine-Containing Amino Acids. Synthesis and Properties; Kukhar', V. P.; Soloshonok, V. A., Eds.; John Wiley & Sons: Chichester, 1994; Chapter 5. (d) Soloshonok, V. A. In Biomedical Frontiers of Fluorine Chemistry; Ojima, I.; McCarthy, J. R.; Welch, J. T., Eds.; ACS Books, American Chemical Society: Washington, DC, 1996; Chapter 2. (e) Soloshonok, V. A. In Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedicinal Targets; Soloshonok, V. A. Ed.; John Wiley & Sons: Chichester, 1999; Chapter 7.
20. For successive papers, see: (a) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Tararov, V. I.; Savel'eva, T. F.; Churkina, T. D.; Ikonnikov, N. S.; Kochetkov, K. A.; Orlova, S. A.; Pysarevsky, A. P.; Struchkov, Yu. T.; Raevsky, N. I.; Belokon', Yu. N. Tetrahedron: Asymmetry 1995, 6, 1741. (b) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P. Tetrahedron: Asymmetry 1996, 7, 1547. (c) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P. Tetrahedron 1996, 52, 12433. De, B. B.; Thomas, N. R. Tetrahedron: Asymmetry 1997, 8, 2687. (e) Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V.; Mischenko, N. Tetrahedron 1999, 55, 12031. (f) Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V. Tetrahedron 1999, 55, 12045. (g) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron: Asymmetry 1999, 10, 4265. (h) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron Lett. 2000, 41, 135. (i) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Organic Lett. 2000, 2, 747. (j) Qiu, W.; Soloshonok, V. A.; Cai, C.; Tang, X.; Hruby, V. J. Tetrahedron 2000, 56, 2577. (k) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Angew. Chem., Int. Ed. 2000, 39, 2172.
21. For successive papers, see: (a) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Tararov, V. I.; Savel'eva, T. F.; Churkina, T. D.; Ikonnikov, N. S.; Kochetkov, K. A.; Orlova, S. A.; Pysarevsky, A. P.; Struchkov, Yu. T.; Raevsky, N. I.; Belokon', Yu. N. Tetrahedron: Asymmetry 1995, 6, 1741. (b) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P. Tetrahedron: Asymmetry 1996, 7, 1547. (c) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P. Tetrahedron 1996, 52, 12433. De, B. B.; Thomas, N. R. Tetrahedron: Asymmetry 1997, 8, 2687. (e) Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V.; Mischenko, N. Tetrahedron 1999, 55, 12031. (f) Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V. Tetrahedron 1999, 55, 12045. (g) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron: Asymmetry 1999, 10, 4265. (h) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron Lett. 2000, 41, 135. (i) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Organic Lett. 2000, 2, 747. (j) Qiu, W.; Soloshonok, V. A.; Cai, C.; Tang, X.; Hruby, V. J. Tetrahedron 2000, 56, 2577. (k) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Angew. Chem., Int. Ed. 2000, 39, 2172.
22. For successive papers, see: (a) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Tararov, V. I.; Savel'eva, T. F.; Churkina, T. D.; Ikonnikov, N. S.; Kochetkov, K. A.; Orlova, S. A.; Pysarevsky, A. P.; Struchkov, Yu. T.; Raevsky, N. I.; Belokon', Yu. N. Tetrahedron: Asymmetry 1995, 6, 1741. (b) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P. Tetrahedron: Asymmetry 1996, 7, 1547. (c) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P. Tetrahedron 1996, 52, 12433. De, B. B.; Thomas, N. R. Tetrahedron: Asymmetry 1997, 8, 2687. (e) Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V.; Mischenko, N. Tetrahedron 1999, 55, 12031. (f) Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V. Tetrahedron 1999, 55, 12045. (g) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron: Asymmetry 1999, 10, 4265. (h) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron Lett. 2000, 41, 135. (i) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Organic Lett. 2000, 2, 747. (j) Qiu, W.; Soloshonok, V. A.; Cai, C.; Tang, X.; Hruby, V. J. Tetrahedron 2000, 56, 2577. (k) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Angew. Chem., Int. Ed. 2000, 39, 2172.
23. For successive papers, see: (a) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Tararov, V. I.; Savel'eva, T. F.; Churkina, T. D.; Ikonnikov, N. S.; Kochetkov, K. A.; Orlova, S. A.; Pysarevsky, A. P.; Struchkov, Yu. T.; Raevsky, N. I.; Belokon', Yu. N. Tetrahedron: Asymmetry 1995, 6, 1741. (b) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P. Tetrahedron: Asymmetry 1996, 7, 1547. (c) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P. Tetrahedron 1996, 52, 12433. De, B. B.; Thomas, N. R. Tetrahedron: Asymmetry 1997, 8, 2687. (e) Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V.; Mischenko, N. Tetrahedron 1999, 55, 12031. (f) Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V. Tetrahedron 1999, 55, 12045. (g) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron: Asymmetry 1999, 10, 4265. (h) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron Lett. 2000, 41, 135. (i) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Organic Lett. 2000, 2, 747. (j) Qiu, W.; Soloshonok, V. A.; Cai, C.; Tang, X.; Hruby, V. J. Tetrahedron 2000, 56, 2577. (k) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Angew. Chem., Int. Ed. 2000, 39, 2172.
24. For successive papers, see: (a) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Tararov, V. I.; Savel'eva, T. F.; Churkina, T. D.; Ikonnikov, N. S.; Kochetkov, K. A.; Orlova, S. A.; Pysarevsky, A. P.; Struchkov, Yu. T.; Raevsky, N. I.; Belokon', Yu. N. Tetrahedron: Asymmetry 1995, 6, 1741. (b) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P. Tetrahedron: Asymmetry 1996, 7, 1547. (c) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P. Tetrahedron 1996, 52, 12433. De, B. B.; Thomas, N. R. Tetrahedron: Asymmetry 1997, 8, 2687. (e) Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V.; Mischenko, N. Tetrahedron 1999, 55, 12031. (f) Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V. Tetrahedron 1999, 55, 12045. (g) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron: Asymmetry 1999, 10, 4265. (h) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron Lett. 2000, 41, 135. (i) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Organic Lett. 2000, 2, 747. (j) Qiu, W.; Soloshonok, V. A.; Cai, C.; Tang, X.; Hruby, V. J. Tetrahedron 2000, 56, 2577. (k) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Angew. Chem., Int. Ed. 2000, 39, 2172.
25. For successive papers, see: (a) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Tararov, V. I.; Savel'eva, T. F.; Churkina, T. D.; Ikonnikov, N. S.; Kochetkov, K. A.; Orlova, S. A.; Pysarevsky, A. P.; Struchkov, Yu. T.; Raevsky, N. I.; Belokon', Yu. N. Tetrahedron: Asymmetry 1995, 6, 1741. (b) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P. Tetrahedron: Asymmetry 1996, 7, 1547. (c) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P. Tetrahedron 1996, 52, 12433. De, B. B.; Thomas, N. R. Tetrahedron: Asymmetry 1997, 8, 2687. (e) Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V.; Mischenko, N. Tetrahedron 1999, 55, 12031. (f) Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V. Tetrahedron 1999, 55, 12045. (g) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron: Asymmetry 1999, 10, 4265. (h) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron Lett. 2000, 41, 135. (i) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Organic Lett. 2000, 2, 747. (j) Qiu, W.; Soloshonok, V. A.; Cai, C.; Tang, X.; Hruby, V. J. Tetrahedron 2000, 56, 2577. (k) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Angew. Chem., Int. Ed. 2000, 39, 2172.
26. For successive papers, see: (a) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Tararov, V. I.; Savel'eva, T. F.; Churkina, T. D.; Ikonnikov, N. S.; Kochetkov, K. A.; Orlova, S. A.; Pysarevsky, A. P.; Struchkov, Yu. T.; Raevsky, N. I.; Belokon', Yu. N. Tetrahedron: Asymmetry 1995, 6, 1741. (b) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P. Tetrahedron: Asymmetry 1996, 7, 1547. (c) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P. Tetrahedron 1996, 52, 12433. De, B. B.; Thomas, N. R. Tetrahedron: Asymmetry 1997, 8, 2687. (e) Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V.; Mischenko, N. Tetrahedron 1999, 55, 12031. (f) Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V. Tetrahedron 1999, 55, 12045. (g) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron: Asymmetry 1999, 10, 4265. (h) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron Lett. 2000, 41, 135. (i) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Organic Lett. 2000, 2, 747. (j) Qiu, W.; Soloshonok, V. A.; Cai, C.; Tang, X.; Hruby, V. J. Tetrahedron 2000, 56, 2577. (k) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Angew. Chem., Int. Ed. 2000, 39, 2172.
27. For successive papers, see: (a) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Tararov, V. I.; Savel'eva, T. F.; Churkina, T. D.; Ikonnikov, N. S.; Kochetkov, K. A.; Orlova, S. A.; Pysarevsky, A. P.; Struchkov, Yu. T.; Raevsky, N. I.; Belokon', Yu. N. Tetrahedron: Asymmetry 1995, 6, 1741. (b) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P. Tetrahedron: Asymmetry 1996, 7, 1547. (c) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P. Tetrahedron 1996, 52, 12433. De, B. B.; Thomas, N. R. Tetrahedron: Asymmetry 1997, 8, 2687. (e) Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V.; Mischenko, N. Tetrahedron 1999, 55, 12031. (f) Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V. Tetrahedron 1999, 55, 12045. (g) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron: Asymmetry 1999, 10, 4265. (h) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron Lett. 2000, 41, 135. (i) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Organic Lett. 2000, 2, 747. (j) Qiu, W.; Soloshonok, V. A.; Cai, C.; Tang, X.; Hruby, V. J. Tetrahedron 2000, 56, 2577. (k) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Angew. Chem., Int. Ed. 2000, 39, 2172.
28. For successive papers, see: (a) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Tararov, V. I.; Savel'eva, T. F.; Churkina, T. D.; Ikonnikov, N. S.; Kochetkov, K. A.; Orlova, S. A.; Pysarevsky, A. P.; Struchkov, Yu. T.; Raevsky, N. I.; Belokon', Yu. N. Tetrahedron: Asymmetry 1995, 6, 1741. (b) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P. Tetrahedron: Asymmetry 1996, 7, 1547. (c) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P. Tetrahedron 1996, 52, 12433. De, B. B.; Thomas, N. R. Tetrahedron: Asymmetry 1997, 8, 2687. (e) Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V.; Mischenko, N. Tetrahedron 1999, 55, 12031. (f) Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V. Tetrahedron 1999, 55, 12045. (g) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron: Asymmetry 1999, 10, 4265. (h) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron Lett. 2000, 41, 135. (i) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Organic Lett. 2000, 2, 747. (j) Qiu, W.; Soloshonok, V. A.; Cai, C.; Tang, X.; Hruby, V. J. Tetrahedron 2000, 56, 2577. (k) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Angew. Chem., Int. Ed. 2000, 39, 2172.
29. For successive papers, see: (a) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Tararov, V. I.; Savel'eva, T. F.; Churkina, T. D.; Ikonnikov, N. S.; Kochetkov, K. A.; Orlova, S. A.; Pysarevsky, A. P.; Struchkov, Yu. T.; Raevsky, N. I.; Belokon', Yu. N. Tetrahedron: Asymmetry 1995, 6, 1741. (b) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P. Tetrahedron: Asymmetry 1996, 7, 1547. (c) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P. Tetrahedron 1996, 52, 12433. De, B. B.; Thomas, N. R. Tetrahedron: Asymmetry 1997, 8, 2687. (e) Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V.; Mischenko, N. Tetrahedron 1999, 55, 12031. (f) Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V. Tetrahedron 1999, 55, 12045. (g) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron: Asymmetry 1999, 10, 4265. (h) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron Lett. 2000, 41, 135. (i) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Organic Lett. 2000, 2, 747. (j) Qiu, W.; Soloshonok, V. A.; Cai, C.; Tang, X.; Hruby, V. J. Tetrahedron 2000, 56, 2577. (k) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Angew. Chem., Int. Ed. 2000, 39, 2172.
30. For successive papers, see: (a) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P.; Tararov, V. I.; Savel'eva, T. F.; Churkina, T. D.; Ikonnikov, N. S.; Kochetkov, K. A.; Orlova, S. A.; Pysarevsky, A. P.; Struchkov, Yu. T.; Raevsky, N. I.; Belokon', Yu. N. Tetrahedron: Asymmetry 1995, 6, 1741. (b) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P. Tetrahedron: Asymmetry 1996, 7, 1547. (c) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P. Tetrahedron 1996, 52, 12433. De, B. B.; Thomas, N. R. Tetrahedron: Asymmetry 1997, 8, 2687. (e) Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V.; Mischenko, N. Tetrahedron 1999, 55, 12031. (f) Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V. Tetrahedron 1999, 55, 12045. (g) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron: Asymmetry 1999, 10, 4265. (h) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron Lett. 2000, 41, 135. (i) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Organic Lett. 2000, 2, 747. (j) Qiu, W.; Soloshonok, V. A.; Cai, C.; Tang, X.; Hruby, V. J. Tetrahedron 2000, 56, 2577. (k) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Angew. Chem., Int. Ed. 2000, 39, 2172.
31. Outcalt, R. J.; Wu, T. T.; Cooke, K. B.; Larochelle, D. J. Agric. Food Chem. 1987, 35, 836.
32. 1H NMR (500 MHz) on the crude reaction mixture.
33. 1H NMR spectra of the complexes containing α-(L)- and α-(D)-amino acids are also very characteristic, featuring substantial difference in chemical shifts of aromatic and methylene protons of the (N-benzyl)proline moiety.