Chiral relay auxiliary for the synthesis of enantiomerically pure α-amino acids

Chemical Communications

Volumn , Issue 6, 1998, Pages 659-660

  Bull, Steven D ^a   Davies, Stephen G ^a   Epstein, Simon W ^a   Ouzman, Jacqueline V A ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002776216     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a800407b     Document Type: Article

References (18)

1. R. M. Williams, Synthesis of Optically Active α-amino acids, Pergamon Press, Oxford, 1989;
2. R. O. Duthaler, Tetrahedron, 1994, 50, 1539.
3. Some of the more popular methods are (a) Seebach's imidazolidinone: D. Seebach, A. R. Sting and M. Hoffmann, Angew. Chem., Int. Ed. Engl., 1997, 35, 2708;
4. (b) Williams' oxazinone: R. M. Williams and M. N. Im, J. Am. Chem. Soc., 1991, 113, 9276;
5. Evans' oxazolidinone: D. A. Evans, A. E. Weber, J. Am. Chem. Soc., 1986, 108, 6757;
6. Oppolzers' sultam: W. Oppolzer, R. Moretti and C. Zhou, Helv. Chim. Acta., 1994, 77, 2363;
7. (e) Myers' pseudoephedrine auxiliary: A. G. Myers, J. L. Gleason and T. Yoon, J. Am. Chem. Soc., 1995, 117, 8488.
8. C. Deng, U. Groth and U. Schöllkopf, Angew. Chem., Int. Ed. Engl., 1981, 20, 798.
9. S. D. Bull, S. G. Davies and W. O. Moss, Tetrahedron: Asymmetry, 1997, in the press.
10. G. Porzi and S. Sandri, Tetrahedron: Asymmetry, 1996, 7, 189.
11. Molecular modelling calculations were carried out using the MOPAC™ (CHEM3D™) suite of Molecular Mechanics programs using PM3 parameters.
12. W. H. Pirkle and P. E. Adams, J. Org. Chem., 1980, 45, 4117.
13. R. M. Williams, M. R. Sabol, H. Kim and A. Kwast, J. Am. Chem. Soc., 1991, 113, 6621.
14. S. Moor and W. H. Stein, J. Biol. Chem., 1951, 192, 663.
15. Identical specific rotation to an authentic sample purchased from Aldrich Chemical Company.
16. W. Karnbrock, H. J. Musiol and L. Moroder, Tetrahedron, 1995, 51, 1187.
17. Only starting material 1 was obtained due to deprotonation of the electrophile.
18. All new compounds were fully characterised.