Dynamic kinetic resolution of α-bromo amides for asymmetric syntheses of di- and tripeptide analogues

Tetrahedron Letters

Volumn 44, Issue 42, 2003, Pages 7727-7730

  Nam, Jiyoun ^a   Chang, Ji Yeon ^a   Hahm, Kyung Soo ^b   Park, Yong Sun ^a  

^a Konkuk University   (South Korea)

^b Chosun University   (South Korea)

Author keywords

Asymmetric syntheses; Dynamic kinetic resolution; Nucleophilic substitution; Peptidomimetics

Indexed keywords

AMIDE; DIBENZYLAMINE; DIPEPTIDE; ESTER DERIVATIVE; LEUCINE; N (ALPHA BROMO ALPHA PHENYLACETYL)ALANINE METHYL ESTER; PROLINE; TRIPEPTIDE; UNCLASSIFIED DRUG;

AMINO TERMINAL SEQUENCE; ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; KINETICS; MOLECULAR DYNAMICS; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0141682290     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.08.091     Document Type: Article

References (21)

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10. For reviews on chiral auxiliary mediated dynamic resolution of α-halo amide, see: (a) Lee, S.-k.; Lee, S. Y.; Park, Y. S. Synlett 2001, 1941; (b) Ward, R. S.; Pelter, A.; Goubet, D.; Pritchard, M. C. Tetrahedron: Asymmetry 1995, 6, 469.
11. For reviews on chiral auxiliary mediated dynamic resolution of α-halo amide, see: (a) Lee, S.-k.; Lee, S. Y.; Park, Y. S. Synlett 2001, 1941; (b) Ward, R. S.; Pelter, A.; Goubet, D.; Pritchard, M. C. Tetrahedron: Asymmetry 1995, 6, 469.
12. 1H NMR of authentic epimers prepared from commercially available (R)-phenylglycine. Those of 21-26 were assigned by analogy to the formation of 13c and 14b . The absolute configurations of two isomers of 13c were confirmed by comparison of Chiral-HPLC retention time with authentic material individually prepared from the coupling of L-leucine derivative and (S)- or (R)-phenylglycine derivative using racemic material as a standard. [Chiralcel OD column; 5% 2-propanol in hexane; 0.5 mL/min; major diastereomer had a retention time of 14.8 min, minor diastereomer had a retention time of 14.1 min.].
13. 4]).
14. 6a-f.
15. Two limiting pathways can be envisaged for dynamic resolution in nucleophilic substitution of α-bromo carboxylic acid derivatives. In one pathway, α-bromo stereogenic center undergoes rapid epimerization and one of the two diastereomers reacts preferentially under the reaction condition. This is a case of dynamic kinetic resolution, in which the stereoselectivity is determined by the difference in the diastereomeric transition state energies for the reaction with the nucleophiles. In a different pathway, the stereoselectivity of the reaction is determined by the ratio of the diastereomers that is established before the substitution. This is termed dynamic thermodynamic resolution because the ratio of diastereomer is thermodynamically controlled and the stereoselectivity of the reaction is not determined by the difference in the rates of substitutions. For reviews on dynamic kinetic resolution in nucleophilic substitution of α-bromo carboxylic acid derivatives, see: (a) Caddick, S.; Afonso, C. A. M.; Candeias, S. X.; Hitchcock, P. B.; Jenkins, K.; Murtagh, L.; Pardoe, D.; Santos A. G.; Treweeke, N. R.; Weaving, R. Tetrahedron 2001, 57, 6589; (b) Ben, R. N.; Durst, T. J. Org. Chem. 1999, 64, 7700; (c) Kubo, A.; Kubota, H.; Takahashi, M.; Nunami, K. J. Org. Chem. 1997, 62, 5830. For reviews on dynamic thermodynamic resolution in nucleophilc substitution of α-bromo carboxylic acid derivatives, see: (d) Nam, J.; Lee, S.-k.; Park, Y. S. Tetrahedron 2003, 59, 2397; (e) Nam, J.; Lee, S.-k.; Kim, K. Y.; Park, Y. S. Tetrahedron Lett. 2002, 43, 8253; (f) Lee, S.-k.; Nam, J.; Park, Y. S. Synlett 2002, 790.
16. Two limiting pathways can be envisaged for dynamic resolution in nucleophilic substitution of α-bromo carboxylic acid derivatives. In one pathway, α-bromo stereogenic center undergoes rapid epimerization and one of the two diastereomers reacts preferentially under the reaction condition. This is a case of dynamic kinetic resolution, in which the stereoselectivity is determined by the difference in the diastereomeric transition state energies for the reaction with the nucleophiles. In a different pathway, the stereoselectivity of the reaction is determined by the ratio of the diastereomers that is established before the substitution. This is termed dynamic thermodynamic resolution because the ratio of diastereomer is thermodynamically controlled and the stereoselectivity of the reaction is not determined by the difference in the rates of substitutions. For reviews on dynamic kinetic resolution in nucleophilic substitution of α-bromo carboxylic acid derivatives, see: (a) Caddick, S.; Afonso, C. A. M.; Candeias, S. X.; Hitchcock, P. B.; Jenkins, K.; Murtagh, L.; Pardoe, D.; Santos A. G.; Treweeke, N. R.; Weaving, R. Tetrahedron 2001, 57, 6589; (b) Ben, R. N.; Durst, T. J. Org. Chem. 1999, 64, 7700; (c) Kubo, A.; Kubota, H.; Takahashi, M.; Nunami, K. J. Org. Chem. 1997, 62, 5830. For reviews on dynamic thermodynamic resolution in nucleophilc substitution of α-bromo carboxylic acid derivatives, see: (d) Nam, J.; Lee, S.-k.; Park, Y. S. Tetrahedron 2003, 59, 2397; (e) Nam, J.; Lee, S.-k.; Kim, K. Y.; Park, Y. S. Tetrahedron Lett. 2002, 43, 8253; (f) Lee, S.-k.; Nam, J.; Park, Y. S. Synlett 2002, 790.
17. Two limiting pathways can be envisaged for dynamic resolution in nucleophilic substitution of α-bromo carboxylic acid derivatives. In one pathway, α-bromo stereogenic center undergoes rapid epimerization and one of the two diastereomers reacts preferentially under the reaction condition. This is a case of dynamic kinetic resolution, in which the stereoselectivity is determined by the difference in the diastereomeric transition state energies for the reaction with the nucleophiles. In a different pathway, the stereoselectivity of the reaction is determined by the ratio of the diastereomers that is established before the substitution. This is termed dynamic thermodynamic resolution because the ratio of diastereomer is thermodynamically controlled and the stereoselectivity of the reaction is not determined by the difference in the rates of substitutions. For reviews on dynamic kinetic resolution in nucleophilic substitution of α-bromo carboxylic acid derivatives, see: (a) Caddick, S.; Afonso, C. A. M.; Candeias, S. X.; Hitchcock, P. B.; Jenkins, K.; Murtagh, L.; Pardoe, D.; Santos A. G.; Treweeke, N. R.; Weaving, R. Tetrahedron 2001, 57, 6589; (b) Ben, R. N.; Durst, T. J. Org. Chem. 1999, 64, 7700; (c) Kubo, A.; Kubota, H.; Takahashi, M.; Nunami, K. J. Org. Chem. 1997, 62, 5830. For reviews on dynamic thermodynamic resolution in nucleophilc substitution of α-bromo carboxylic acid derivatives, see: (d) Nam, J.; Lee, S.-k.; Park, Y. S. Tetrahedron 2003, 59, 2397; (e) Nam, J.; Lee, S.-k.; Kim, K. Y.; Park, Y. S. Tetrahedron Lett. 2002, 43, 8253; (f) Lee, S.-k.; Nam, J.; Park, Y. S. Synlett 2002, 790.
18. Two limiting pathways can be envisaged for dynamic resolution in nucleophilic substitution of α-bromo carboxylic acid derivatives. In one pathway, α-bromo stereogenic center undergoes rapid epimerization and one of the two diastereomers reacts preferentially under the reaction condition. This is a case of dynamic kinetic resolution, in which the stereoselectivity is determined by the difference in the diastereomeric transition state energies for the reaction with the nucleophiles. In a different pathway, the stereoselectivity of the reaction is determined by the ratio of the diastereomers that is established before the substitution. This is termed dynamic thermodynamic resolution because the ratio of diastereomer is thermodynamically controlled and the stereoselectivity of the reaction is not determined by the difference in the rates of substitutions. For reviews on dynamic kinetic resolution in nucleophilic substitution of α-bromo carboxylic acid derivatives, see: (a) Caddick, S.; Afonso, C. A. M.; Candeias, S. X.; Hitchcock, P. B.; Jenkins, K.; Murtagh, L.; Pardoe, D.; Santos A. G.; Treweeke, N. R.; Weaving, R. Tetrahedron 2001, 57, 6589; (b) Ben, R. N.; Durst, T. J. Org. Chem. 1999, 64, 7700; (c) Kubo, A.; Kubota, H.; Takahashi, M.; Nunami, K. J. Org. Chem. 1997, 62, 5830. For reviews on dynamic thermodynamic resolution in nucleophilc substitution of α-bromo carboxylic acid derivatives, see: (d) Nam, J.; Lee, S.-k.; Park, Y. S. Tetrahedron 2003, 59, 2397; (e) Nam, J.; Lee, S.-k.; Kim, K. Y.; Park, Y. S. Tetrahedron Lett. 2002, 43, 8253; (f) Lee, S.-k.; Nam, J.; Park, Y. S. Synlett 2002, 790.
19. Two limiting pathways can be envisaged for dynamic resolution in nucleophilic substitution of α-bromo carboxylic acid derivatives. In one pathway, α-bromo stereogenic center undergoes rapid epimerization and one of the two diastereomers reacts preferentially under the reaction condition. This is a case of dynamic kinetic resolution, in which the stereoselectivity is determined by the difference in the diastereomeric transition state energies for the reaction with the nucleophiles. In a different pathway, the stereoselectivity of the reaction is determined by the ratio of the diastereomers that is established before the substitution. This is termed dynamic thermodynamic resolution because the ratio of diastereomer is thermodynamically controlled and the stereoselectivity of the reaction is not determined by the difference in the rates of substitutions. For reviews on dynamic kinetic resolution in nucleophilic substitution of α-bromo carboxylic acid derivatives, see: (a) Caddick, S.; Afonso, C. A. M.; Candeias, S. X.; Hitchcock, P. B.; Jenkins, K.; Murtagh, L.; Pardoe, D.; Santos A. G.; Treweeke, N. R.; Weaving, R. Tetrahedron 2001, 57, 6589; (b) Ben, R. N.; Durst, T. J. Org. Chem. 1999, 64, 7700; (c) Kubo, A.; Kubota, H.; Takahashi, M.; Nunami, K. J. Org. Chem. 1997, 62, 5830. For reviews on dynamic thermodynamic resolution in nucleophilc substitution of α-bromo carboxylic acid derivatives, see: (d) Nam, J.; Lee, S.-k.; Park, Y. S. Tetrahedron 2003, 59, 2397; (e) Nam, J.; Lee, S.-k.; Kim, K. Y.; Park, Y. S. Tetrahedron Lett. 2002, 43, 8253; (f) Lee, S.-k.; Nam, J.; Park, Y. S. Synlett 2002, 790.
20. Two limiting pathways can be envisaged for dynamic resolution in nucleophilic substitution of α-bromo carboxylic acid derivatives. In one pathway, α-bromo stereogenic center undergoes rapid epimerization and one of the two diastereomers reacts preferentially under the reaction condition. This is a case of dynamic kinetic resolution, in which the stereoselectivity is determined by the difference in the diastereomeric transition state energies for the reaction with the nucleophiles. In a different pathway, the stereoselectivity of the reaction is determined by the ratio of the diastereomers that is established before the substitution. This is termed dynamic thermodynamic resolution because the ratio of diastereomer is thermodynamically controlled and the stereoselectivity of the reaction is not determined by the difference in the rates of substitutions. For reviews on dynamic kinetic resolution in nucleophilic substitution of α-bromo carboxylic acid derivatives, see: (a) Caddick, S.; Afonso, C. A. M.; Candeias, S. X.; Hitchcock, P. B.; Jenkins, K.; Murtagh, L.; Pardoe, D.; Santos A. G.; Treweeke, N. R.; Weaving, R. Tetrahedron 2001, 57, 6589; (b) Ben, R. N.; Durst, T. J. Org. Chem. 1999, 64, 7700; (c) Kubo, A.; Kubota, H.; Takahashi, M.; Nunami, K. J. Org. Chem. 1997, 62, 5830. For reviews on dynamic thermodynamic resolution in nucleophilc substitution of α-bromo carboxylic acid derivatives, see: (d) Nam, J.; Lee, S.-k.; Park, Y. S. Tetrahedron 2003, 59, 2397; (e) Nam, J.; Lee, S.-k.; Kim, K. Y.; Park, Y. S. Tetrahedron Lett. 2002, 43, 8253; (f) Lee, S.-k.; Nam, J.; Park, Y. S. Synlett 2002, 790.
21. 1H NMR and Chiral-HPLC, which can rule out the possibility of epimerization after the replacement of Br with dibenzylamine in the stereoselective nucleophilic substitution reaction.