Enantiospecific synthesis of (R)- and (S)-2,3-diaminopropanol from L- and D-serine

Synthesis

Volumn , Issue 2, 1996, Pages 189-191

  Demirci, Fatih ^a   Haines, Alan H ^a   Jia, Chunhua ^a   Wu, Di ^a  

^a UNIVERSITY OF EAST ANGLIA   (United Kingdom)

Author keywords

2,3 diaminopropanol; chiral; enantiospecific; serine

Indexed keywords

2,3 DIAMINOPROPANOL; DIAMINE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030007305     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4198     Document Type: Article

References (13)

1. Jia, C.; Haines, A. H. J. Chem. Soc., Perkin Trans. I 1993, 2521.
2. Okamoto, M. S.; Barefield, E. K. Inorg. Chem. 1974, 13, 2611.
3. Noji, M.; Motoyama, S.; Tashiro, T.; Kidani, Y. Chem. Pharm. Bull. 1983, 31, 1469. It should be noted that this reference ascribes the R and S descriptors to the positively and negatively rotating dihydrochlorides of 6, respectively.
4. Holmes, D. S.; Clemens, I. R.; Cobley, K. N.; Humber, D. C.; Kitchin, J.; Orr, D. C.; Patel, B.; Pasternoster, I.; Storer, R. Bioorg. Med. Chem. Lett. 1993, 3, 503.
5. Golding, B. T.; Howes, C. J. Chem. Res. (S) 1984, 1.
6. Hassall, C. H.; Thomas, J. O. J. Chem. Soc. (C) 1968, 1495.
7. Brands, K. M. J.; Meekel, A. A. P.; Pandit, U. K. Tetrahedron 1991, 47, 2005.
8. (S)-2,3-Diaminopropanol (S-6) was similarly prepared as its dihydrochloride using N-benzyloxycarbonl-D-serine methyl ester (R-1) as the starting material.
9. The NMR spectra of all of the compounds containing the N-benzyloxycarbonyl group, except for R-1 and 5-1, showed effects attributable to restricted rotation about the amide bond, for example peak doubling or broadening.
10. The complete synthetic sequence to prepare 2,3-diaminopropanol (6) was performed also with racemic material but the experimental details are omitted here.
11. Viaud, M. C.; Rollin, P. Synthesis 1990, 130.
12. 5
13. Cossu, S.; Giacomelli, G.; Conti, S.; Falorni, M. Tetrahedron 1994, 50, 5083.