Asymmetric syntheses of α-mercapto carboxylic acid derivatives by dynamic resolution of N-methyl pseudoephedrine α-bromo esters

Tetrahedron Letters

Volumn 43, Issue 46, 2002, Pages 8253-8255

  Nam, Jiyoun ^a   Lee, Sang kuk ^a   Kim, Kee Yong ^a   Park, Yong Sun ^a  

^a Konkuk University   (South Korea)

Author keywords

mercapto carboxylic acids; Asymmetric synthesis; Chiral auxiliaries; Dynamic resolution

Indexed keywords

ALCOHOL DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE; SULFUR DERIVATIVE; THIOL DERIVATIVE;

ALCOHOLYSIS; ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; CHIRALITY; EPIMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIZATION; THERMODYNAMICS;

EID: 0037064498     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02020-8     Document Type: Article

References (16)

1. Cohen D.S., Fink C.A., Trapani A.J., Webb R.L., Zane P.A., Chatelain R.E. Cardiovasc. Drug Rev. 17:1999;16.
2. Gaucher J.F., Selkti M., Tiraboschi G., Prangé T., Roques B.P., Tomas A., Fournié-Zaluski M.C. Biochemistry. 38:1999;12569.
3. Bohacek R., Lombaert S.D., McMartin C., Priestle J., Grütter M. J. Am. Chem. Soc. 118:1996;8231.
4. Lee S.-K., Lee S.Y., Park Y.S. Synlett. 2001;1941.
5. Schedel H., Quaedflieg P.J.L.M., Broxtermann Q.B., Bisson W., Duchateau A.L.L., Maes I.C.H., Herzschuh R., Burger K. Tetrahedron: Asymmetry. 11:2000;2125.
6. Harding R.L., Bugg T.D.H. Tetrahedron Lett. 41:2000;2729.
7. Chen B.-C., Bednarz M.S., Kocy O.R., Sundeen J.E. Tetrahedron: Asymmetry. 9:1998;1641.
8. Kelly S.E., LaCour T.G. Tetrahedron: Asymmetry. 3:1992;715.
9. Strijtveen B., Kellogg R.M. J. Org. Chem. 51:1986;3664.
10. For asymmetric syntheses of α-amino and α-hydroxy carboxylic acids via dynamic resolution of α-halo carboxylic acid derivatives, see: (a) Ben, R. N.; Durst, T. J. Org. Chem. 1999, 64, 7700; (b) Kubo, A.; Kubota, H.; Takahashi, M.; Nunami, K. J. Org. Chem. 1997, 62, 5830; (c) Ward, R. S.; Pelter, A.; Goubet, D.; Pritchard, M. C. Tetrahedron: Asymmetry 1995, 6, 469; (d) 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; (e) Lee, S.-K.; Nam, J.; Park, Y. S. Synlett 2002, 790.
11. For asymmetric syntheses of α-amino and α-hydroxy carboxylic acids via dynamic resolution of α-halo carboxylic acid derivatives, see: (a) Ben, R. N.; Durst, T. J. Org. Chem. 1999, 64, 7700; (b) Kubo, A.; Kubota, H.; Takahashi, M.; Nunami, K. J. Org. Chem. 1997, 62, 5830; (c) Ward, R. S.; Pelter, A.; Goubet, D.; Pritchard, M. C. Tetrahedron: Asymmetry 1995, 6, 469; (d) 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; (e) Lee, S.-K.; Nam, J.; Park, Y. S. Synlett 2002, 790.
12. For asymmetric syntheses of α-amino and α-hydroxy carboxylic acids via dynamic resolution of α-halo carboxylic acid derivatives, see: (a) Ben, R. N.; Durst, T. J. Org. Chem. 1999, 64, 7700; (b) Kubo, A.; Kubota, H.; Takahashi, M.; Nunami, K. J. Org. Chem. 1997, 62, 5830; (c) Ward, R. S.; Pelter, A.; Goubet, D.; Pritchard, M. C. Tetrahedron: Asymmetry 1995, 6, 469; (d) 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; (e) Lee, S.-K.; Nam, J.; Park, Y. S. Synlett 2002, 790.
13. For asymmetric syntheses of α-amino and α-hydroxy carboxylic acids via dynamic resolution of α-halo carboxylic acid derivatives, see: (a) Ben, R. N.; Durst, T. J. Org. Chem. 1999, 64, 7700; (b) Kubo, A.; Kubota, H.; Takahashi, M.; Nunami, K. J. Org. Chem. 1997, 62, 5830; (c) Ward, R. S.; Pelter, A.; Goubet, D.; Pritchard, M. C. Tetrahedron: Asymmetry 1995, 6, 469; (d) 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; (e) Lee, S.-K.; Nam, J.; Park, Y. S. Synlett 2002, 790.
14. 3CN).
15. 1H NMR of authentic epimer obtained from the coupling of (S,S)-N-methyl pseudoephedrine and (S)-2-bromobutanoic acid obtained from commercially available (S)-2-aminobutyric acid.
16. 3)