Optimisation of the retroracemisation procedure for α-amino acids using (S)-2-[(N-alkylprolyl)amino]benzophenones, recyclable chiral axiliaries

Tetrahedron Asymmetry

Volumn 8, Issue 16, 1997, Pages 2687-2691

  De, Binod B ^a   Thomas, Neil R ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; BENZOPHENONE DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; DECOMPOSITION; DIASTEREOISOMER; PRIORITY JOURNAL; RACEMIC MIXTURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030886790     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00331-5     Document Type: Article

References (13)

1. For recent comprehensive reviews on asymmetric synthesis of α-amino acids see: Williams, R. M., Synthesis of Optically Active α-Amino Acids, Pergamon Press, Oxford, 1989; Duthaler, R. P. Tetrahedron, 1994, 50, 1539.
2. For recent comprehensive reviews on asymmetric synthesis of α-amino acids see: Williams, R. M., Synthesis of Optically Active α-Amino Acids, Pergamon Press, Oxford, 1989; Duthaler, R. P. Tetrahedron, 1994, 50, 1539.
3. For examples see Chirality in Industry, Collins, A. N.; Sheldrake, G. N.; Crosby, J., Eds; Wiley, Chichester, 1992 (vol. 1), 1997 (vol. 2).
4. Belokon, Y. N.; Zeltzer, I. E.; Bakhmutov, V. I. Saporovskaya, M. B.; Ryzhov, M. G.; Yanovsky, A. I.; Struchkov, Y. T.; Belikov, V. M. J. Am. Chem. Soc., 1983, 105, 2010.
5. Belokon, Y. N. Janssen Chim. Acta, 1992, 10, 4; Belokon, Y. N. Pure Appl. Chem., 1992, 64, 1917; Soloshonak, V. A.; Avilov, D. V.; and Kukhar, V. P. Tetrahedron: Asymmetry, 1996, 7, 1547.
6. Belokon, Y. N. Janssen Chim. Acta, 1992, 10, 4; Belokon, Y. N. Pure Appl. Chem., 1992, 64, 1917; Soloshonak, V. A.; Avilov, D. V.; and Kukhar, V. P. Tetrahedron: Asymmetry, 1996, 7, 1547.
7. Belokon, Y. N. Janssen Chim. Acta, 1992, 10, 4; Belokon, Y. N. Pure Appl. Chem., 1992, 64, 1917; Soloshonak, V. A.; Avilov, D. V.; and Kukhar, V. P. Tetrahedron: Asymmetry, 1996, 7, 1547.
8. 7
9. Available from Merck and Acros Chimica.
10. Available from Daicel Chemical Industries Ltd, Japan.
11. 2), 7.05-8.55 (13H, s, Ar), 9.06 (1H br s, NH).
12. Owa, T.; Otusuka, M.; Ohno, M. Chem. Lett., 1988, 83.
13. Crystals of (S)-2-PCBP:Ni(II):(S)-Phe and (S)-3-PCBP:Ni(II):(S)-Phe were grown up in chloroform. Full crystallographic data for these two compounds have been deposited at the Cambridge Crystallographic Data Centre and are available from the principal author.