Practical resolution of an atropoisomeric α,α-disubstituted glycine with L-phenylalanine cyclohexylamide as chiral auxiliary

Tetrahedron Asymmetry

Volumn 9, Issue 15, 1998, Pages 2701-2713

  Mazaleyrat, Jean Paul ^a   Boutboul, Aurelia ^a   Lebars, Yann ^a   Gaucher, Anne ^a   Wakselman, Michel ^a  

^a LABORATOIRE DES SCIENCES DU CLIMAT ET DE L ENVIRONNEMENT   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CYCLOHEXYLAMINE DERIVATIVE; DIPEPTIDE; GLYCINE DERIVATIVE; NAPHTHYL GROUP; PHENYLALANINE;

ARTICLE; CHIRALITY; COLUMN CHROMATOGRAPHY; CRYSTALLIZATION; DIASTEREOISOMER; ENANTIOMER; ESTERIFICATION; HYDROLYSIS; PRIORITY JOURNAL; RACEMIC MIXTURE; SYNTHESIS;

EID: 0032493841     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00253-5     Document Type: Article

References (22)

1. For some recent leading references on open-chain and cyclic α, α-disubstituted-α-amino acids, see: (a) Toniolo, C. Janssen Chimica Acta 1993, 11(28) 10-16. (b) Benedetti, E. Biopolymers 1996, 40, 3-44. (c) Karle, I. L. Biopolymers 1996, 40, 157-180. (d) Toniolo, C.; Crisma, M.; Formaggio, F.; Benedetti, E.; Santini, A.; Iacovino, R.; Saviano, M.; Di Blasio, B.; Pedone, C.; Kamphuis, J. Biopolymers 1996, 40, 519-522.
2. For some recent leading references on open-chain and cyclic α, α-disubstituted-α-amino acids, see: (a) Toniolo, C. Janssen Chimica Acta 1993, 11(28) 10-16. (b) Benedetti, E. Biopolymers 1996, 40, 3-44. (c) Karle, I. L. Biopolymers 1996, 40, 157-180. (d) Toniolo, C.; Crisma, M.; Formaggio, F.; Benedetti, E.; Santini, A.; Iacovino, R.; Saviano, M.; Di Blasio, B.; Pedone, C.; Kamphuis, J. Biopolymers 1996, 40, 519-522.
3. For some recent leading references on open-chain and cyclic α, α-disubstituted-α-amino acids, see: (a) Toniolo, C. Janssen Chimica Acta 1993, 11(28) 10-16. (b) Benedetti, E. Biopolymers 1996, 40, 3-44. (c) Karle, I. L. Biopolymers 1996, 40, 157-180. (d) Toniolo, C.; Crisma, M.; Formaggio, F.; Benedetti, E.; Santini, A.; Iacovino, R.; Saviano, M.; Di Blasio, B.; Pedone, C.; Kamphuis, J. Biopolymers 1996, 40, 519-522.
4. For some recent leading references on open-chain and cyclic α, α-disubstituted-α-amino acids, see: (a) Toniolo, C. Janssen Chimica Acta 1993, 11(28) 10-16. (b) Benedetti, E. Biopolymers 1996, 40, 3-44. (c) Karle, I. L. Biopolymers 1996, 40, 157-180. (d) Toniolo, C.; Crisma, M.; Formaggio, F.; Benedetti, E.; Santini, A.; Iacovino, R.; Saviano, M.; Di Blasio, B.; Pedone, C.; Kamphuis, J. Biopolymers 1996, 40, 519-522.
5. (a) Mazaleyrat, J.-P.; Gaucher, A.; Wakselman, M.; Tchertanov, L.; Guilhem, J. Tetrahedron Lett. 1996, 37, 2971-2974.
6. (b) Mazaleyrat, J.-P.; Gaucher, A.; Šavrda, J.; Wakselman, M. Tetrahedron: Asymmetry 1997, 8, 619-631.
7. (a) Mazaleyrat, J.-P.; Gaucher, A.; Wakselman, M.; Toniolo, C.; Crisma, M.; Formaggio, F. Peptides 1996, R. Ramage and R. Epton, Eds.; Mayflower Worldwide 1997, in press.
8. (b) Toniolo, C.; Crisma, M.; Formaggio, F.; Pispisa, B.; Flippen-Anderson, J. L.; Mazaleyrat, J. P.; Wakselman, M. Peptides. Chemistry, Structure and Biology. Proceedings of the 15th American Peptide Symposium, 1998, in press.
9. For leading references, see: (a) Toniolo, C.; Crisma, M.; Formaggio, F.; Valle, G.; Cavicchioni, G.; Precigoux, G.; Aubry, A.; Kamphuis, J. Biopolymers 1993, 33, 1061-1072. (b) Crisma, M.; Valle, G.; Pantano, M.; Formaggio, F.; Bonora, G. M.; Toniolo, C.; Kamphuis, J. Recl. Trav. Chim. Pays-Bas 1995, 114, 325-331. (c) Doi, M.; Ishida, T.; Polese, A.; Formaggio, F.; Crisma, M.; Toniolo, C.; Broxterman, Q. B.; Kamphuis, J. Pept. Res. 1995, 8, 294-297. (d) Formaggio, F.; Pantano, M.; Crisma, M.; Bonora, G. M.; Toniolo, C.; Kamphuis, J. J. Chem. Soc., Perkin Trans. 2 1995, 1097-1101. (e) Yoder, G.; Keiderling, T. A.; Formaggio, F.; Crisma, M.; Toniolo, C.; Kamphuis, J. Tetrahedron: Asymmetry 1995, 6, 687-690. (f) Polese, A.; Formaggio, F.; Crisma, M.; Valle, G.; Toniolo, C.; Bonora, G. M.; Broxterman, Q. B.; Kamphuis, J. Chem. Eur. J. 1996, 2, 1104-1111.
10. For leading references, see: (a) Toniolo, C.; Crisma, M.; Formaggio, F.; Valle, G.; Cavicchioni, G.; Precigoux, G.; Aubry, A.; Kamphuis, J. Biopolymers 1993, 33, 1061-1072. (b) Crisma, M.; Valle, G.; Pantano, M.; Formaggio, F.; Bonora, G. M.; Toniolo, C.; Kamphuis, J. Recl. Trav. Chim. Pays-Bas 1995, 114, 325-331. (c) Doi, M.; Ishida, T.; Polese, A.; Formaggio, F.; Crisma, M.; Toniolo, C.; Broxterman, Q. B.; Kamphuis, J. Pept. Res. 1995, 8, 294-297. (d) Formaggio, F.; Pantano, M.; Crisma, M.; Bonora, G. M.; Toniolo, C.; Kamphuis, J. J. Chem. Soc., Perkin Trans. 2 1995, 1097-1101. (e) Yoder, G.; Keiderling, T. A.; Formaggio, F.; Crisma, M.; Toniolo, C.; Kamphuis, J. Tetrahedron: Asymmetry 1995, 6, 687-690. (f) Polese, A.; Formaggio, F.; Crisma, M.; Valle, G.; Toniolo, C.; Bonora, G. M.; Broxterman, Q. B.; Kamphuis, J. Chem. Eur. J. 1996, 2, 1104-1111.
11. For leading references, see: (a) Toniolo, C.; Crisma, M.; Formaggio, F.; Valle, G.; Cavicchioni, G.; Precigoux, G.; Aubry, A.; Kamphuis, J. Biopolymers 1993, 33, 1061-1072. (b) Crisma, M.; Valle, G.; Pantano, M.; Formaggio, F.; Bonora, G. M.; Toniolo, C.; Kamphuis, J. Recl. Trav. Chim. Pays-Bas 1995, 114, 325-331. (c) Doi, M.; Ishida, T.; Polese, A.; Formaggio, F.; Crisma, M.; Toniolo, C.; Broxterman, Q. B.; Kamphuis, J. Pept. Res. 1995, 8, 294-297. (d) Formaggio, F.; Pantano, M.; Crisma, M.; Bonora, G. M.; Toniolo, C.; Kamphuis, J. J. Chem. Soc., Perkin Trans. 2 1995, 1097-1101. (e) Yoder, G.; Keiderling, T. A.; Formaggio, F.; Crisma, M.; Toniolo, C.; Kamphuis, J. Tetrahedron: Asymmetry 1995, 6, 687-690. (f) Polese, A.; Formaggio, F.; Crisma, M.; Valle, G.; Toniolo, C.; Bonora, G. M.; Broxterman, Q. B.; Kamphuis, J. Chem. Eur. J. 1996, 2, 1104-1111.
12. For leading references, see: (a) Toniolo, C.; Crisma, M.; Formaggio, F.; Valle, G.; Cavicchioni, G.; Precigoux, G.; Aubry, A.; Kamphuis, J. Biopolymers 1993, 33, 1061-1072. (b) Crisma, M.; Valle, G.; Pantano, M.; Formaggio, F.; Bonora, G. M.; Toniolo, C.; Kamphuis, J. Recl. Trav. Chim. Pays-Bas 1995, 114, 325-331. (c) Doi, M.; Ishida, T.; Polese, A.; Formaggio, F.; Crisma, M.; Toniolo, C.; Broxterman, Q. B.; Kamphuis, J. Pept. Res. 1995, 8, 294-297. (d) Formaggio, F.; Pantano, M.; Crisma, M.; Bonora, G. M.; Toniolo, C.; Kamphuis, J. J. Chem. Soc., Perkin Trans. 2 1995, 1097-1101. (e) Yoder, G.; Keiderling, T. A.; Formaggio, F.; Crisma, M.; Toniolo, C.; Kamphuis, J. Tetrahedron: Asymmetry 1995, 6, 687-690. (f) Polese, A.; Formaggio, F.; Crisma, M.; Valle, G.; Toniolo, C.; Bonora, G. M.; Broxterman, Q. B.; Kamphuis, J. Chem. Eur. J. 1996, 2, 1104-1111.
13. For leading references, see: (a) Toniolo, C.; Crisma, M.; Formaggio, F.; Valle, G.; Cavicchioni, G.; Precigoux, G.; Aubry, A.; Kamphuis, J. Biopolymers 1993, 33, 1061-1072. (b) Crisma, M.; Valle, G.; Pantano, M.; Formaggio, F.; Bonora, G. M.; Toniolo, C.; Kamphuis, J. Recl. Trav. Chim. Pays-Bas 1995, 114, 325-331. (c) Doi, M.; Ishida, T.; Polese, A.; Formaggio, F.; Crisma, M.; Toniolo, C.; Broxterman, Q. B.; Kamphuis, J. Pept. Res. 1995, 8, 294-297. (d) Formaggio, F.; Pantano, M.; Crisma, M.; Bonora, G. M.; Toniolo, C.; Kamphuis, J. J. Chem. Soc., Perkin Trans. 2 1995, 1097-1101. (e) Yoder, G.; Keiderling, T. A.; Formaggio, F.; Crisma, M.; Toniolo, C.; Kamphuis, J. Tetrahedron: Asymmetry 1995, 6, 687-690. (f) Polese, A.; Formaggio, F.; Crisma, M.; Valle, G.; Toniolo, C.; Bonora, G. M.; Broxterman, Q. B.; Kamphuis, J. Chem. Eur. J. 1996, 2, 1104-1111.
14. For leading references, see: (a) Toniolo, C.; Crisma, M.; Formaggio, F.; Valle, G.; Cavicchioni, G.; Precigoux, G.; Aubry, A.; Kamphuis, J. Biopolymers 1993, 33, 1061-1072. (b) Crisma, M.; Valle, G.; Pantano, M.; Formaggio, F.; Bonora, G. M.; Toniolo, C.; Kamphuis, J. Recl. Trav. Chim. Pays-Bas 1995, 114, 325-331. (c) Doi, M.; Ishida, T.; Polese, A.; Formaggio, F.; Crisma, M.; Toniolo, C.; Broxterman, Q. B.; Kamphuis, J. Pept. Res. 1995, 8, 294-297. (d) Formaggio, F.; Pantano, M.; Crisma, M.; Bonora, G. M.; Toniolo, C.; Kamphuis, J. J. Chem. Soc., Perkin Trans. 2 1995, 1097-1101. (e) Yoder, G.; Keiderling, T. A.; Formaggio, F.; Crisma, M.; Toniolo, C.; Kamphuis, J. Tetrahedron: Asymmetry 1995, 6, 687-690. (f) Polese, A.; Formaggio, F.; Crisma, M.; Valle, G.; Toniolo, C.; Bonora, G. M.; Broxterman, Q. B.; Kamphuis, J. Chem. Eur. J. 1996, 2, 1104-1111.
15. (a) Obrecht, D.; Spiegler, C.; Schönholzer, P.; Müller, K.; Heimgartner, H.; Stierli, F. Helv. Chim. Acta 1992, 75, 1666-1696.
16. (b) Obrecht, D.; Bohdal, U.; Broger, C.; Bur, D.; Lehmann, C.; Ruffieux, R.; Schönholzer, P.; Spiegler, C.; Müller, K. Helv. Chim. Acta 1995, 78, 563-580.
17. Maigrot, N.; Mazaleyrat, J.-P. Synthesis 1985, 317-320.
18. Yield based on the half amount of the starting racemic compound.
19. Tchertanov, L.; Guilhem, J.; Mazaleyrat, J.-P.; Gaucher, A.; Wakselman, M. Acta Cryst. (B) 1998, in press.
20. 2b would lead to Boc (or Z)-Bin-OH as a single product.
21. (a) Hall, D. M.; Turner, E. E. J. Chem. Soc. 1955, 1242-1251.
22. (b) Dixon, W.; Harris, M. M.; Mazengo, R. Z. J. Chem. Soc. (B) 1971, 775-778.