Asymmetric synthesis of arylglycine amino acids using (S,S)-(+)- pseudoephedrine derived amides

Tetrahedron Letters

Volumn 40, Issue 39, 1999, Pages 7123-7126

  Vicario, Jose L ^a   Badia, Dolores ^a   Domínguez, Esther ^a   Crespo, Ana ^a   Carrillo, Luisa ^a   Anakabe, Eneritz ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; GLYCINE DERIVATIVE; PSEUDOEPHEDRINE;

AMINATION; AMINO ACID SYNTHESIS; ARTICLE; HYDROLYSIS; MOLECULAR INTERACTION;

EID: 0033600688     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01475-6     Document Type: Article

References (21)

1. 1. (a) Duthaler, O.R. Tetrahedron 1994, 50, 1539-1650.
2. (b). Studer, A. Synthesis 1996, 793-815.
3. 2. Bedingfield, J.S.; Kemp, M.C.; Jane, D.E.; Tse, H.W.; Roberts, P.J.; Watkins, J. J. Pharmacol. 1995, 116, 3323-3330.
4. 3. For a review on glycopeptide antibiotics see (a) Williams, D.H.; Waltho, J.P. Biochem. Pharmacol. 1988, 37, 133-141.
5. (b) Barna, J.C.; Williams, D.H. Ann. Rev. Microbiol. 1984, 38, 339-357.
6. 4. For recent reviews see (a) Williams, R.M. In Synthesis of Optically Active Amino Acids; Pergamon Press: Oxford, 1989.
7. (b) Seebach, D.; Sting, A.R.; Hoffmann, M. Angew. Chem., Int. Edn. Engl. 1996, 35, 2708-2748.
8. 5. Phenylglycine is times more racemization-prone than alanine: Smith, G.G.; Sivakua, T. J. Org. Chem. 1983, 48, 627-634.
9. 6. For a review: (a) Williams, R.M.; Hendrix, J.A. Chem. Rev. 1992, 92, 889-917.
10. For recent examples see (b) Davis, F.A.; Fanelli, D.L. J. Org. Chem. 1998, 63, 1981-1985.
11. (c) Reddy, K.L.; Sharpless, K.B. J. Am. Chem. Soc. 1998, 120, 1207-1217.
12. (d) Vergne, C.; Bouillon, J.-P.; Chastanet, J.; Bois-Choussy, M.; Zhu, J. Tetrahedron: Asymmetry 1998, 9, 3095-3103.
13. (e) Petasis, N.A.; Goodman, A.; Zavialov, I.A. Tetrahedron 1997, 53, 16463-16470.
14. 7. (a) Carrillo, L.; Badía, D.; Domínguez, E.; Vicario, J. L.; Tellitu, I. J. Org. Chem. 1997, 62, 6716-6721.
15. (b) Carrillo, L.; Badía, D.; Domínguez, E.; Tellitu, I.; Vicario, J. L. Tetrahedron: Asymmetry 1998, 9, 1809-1816.
16. 8. For the use of (S,S)-(+)-pseudoephedrine as chiral auxiliary see Myers, A.G.; Yang, B.H.; Chen, H.; McKinstry, L.; Kopecky, D.J.; Gleason, J.L. J. Am. Chem. Soc. 1997, 119, 6496-6511.
17. 9. Trimble, L.A.; Vederas, J.C. J. Am. Chem. Soc. 1986, 108, 6397-6399.
18. 10. Vicario, J.L.; Badia, D.; Domínguez, E.; Carrillo, L. J. Org. Chem, 1999, in press.
19. 4, filtered and the solvent was removed in vacuo to afford a yellowish oil which was purified by flash column chromatography.
20. 12. Rück, K. Angew. Chem. Int. Edn. Engl 1995, 34, 433-435.
21. 20=+97.6 (c=1.95 EtOH) see ref. 6c.