A simple asymmetric synthesis of (+)- and (-)-2,6-diaminopimelic acids

Tetrahedron Asymmetry

Volumn 11, Issue 6, 2000, Pages 1259-1262

  Paradisi, F ^a   Porzi, G ^a   Rinaldi, S ^a   Sandri, S ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

DIAMINOPIMELIC ACID;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CONFORMATIONAL TRANSITION; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0034616096     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00050-1     Document Type: Article

References (10)

1. Williams, R. M.; Fegley, G. J.; Gallegos, R.; Schaefer, F.; Pruess, D. L. Tetrahedron 1996 , 52, 1149 and references cited therein.
2. Gelb, M. H.; Lçin, Y.; Pickard, M. A.; Song, Y.; Vederas, J. C. J. Am. Chem. Soc. 1990 , 112 , 4932; Williams, R. M.; Im, M.-N.; Cao, J. J. Am. Chem. Soc. 1991 , 113 , 6976; Williams, R. M.; Yuan, C. J. Org. Chem. 1992 , 57 , 6519; Abbott, S. D.; Lane-Bell, P.; Sidhu, K. P. S.; Vederas, J. C. J. Am. Chem. Soc. 1994 , 116 , 6513; Song, Y.; Niederer, D.; Lane-Bell, P. M.; Lan, L. K. P.; Crawley, S.; Palcic, M. M.; Pickard, M. A.; Pruess, D. L.; Vederas, J. C. J. Org. Chem. 1994 , 59 , 5784; Bull, S. D.; Chernega, A. N.; Davies, S. G.; Moss, W. O.; Parkin, R. M. Tetrahedron 1998 , 54 , 10379 and references cited therein.
3. Porzi, G.; Sandri, S. Tetrahedron: Asymmetry 1996 , 7 , 189; Favero, V.; Porzi, G.; Sandri, S. Tetrahedron: Asymmetry 1997 , 8 , 599; Porzi, G.; Sandri, S. Tetrahedron: Asymmetry 1998 , 9 , 3411; Carloni, A.; Porzi, G.; Sandri, S. Tetrahedron: Asymmetry 1998 , 9 , 2987; Di Felice, P.; Maestri, M.; Paradisi, F.; Porzi, G.; Sandri, S. Tetrahedron: Asymmetry 1999 , 10 , 4709.
4. Porzi, G.; Sandri, S. Tetrahedron: Asymmetry 1994 , 5 , 453.
5. 3).
6. 3).
7. 2O vs DSS) 1.4 (m, 2H), 1.8 (m, 4H), 3.7 (m, 2H).
8. Orena, M.; Porzi, G.; Sandri, S. J. Org. Chem. 1992 , 57 , 6532; Orena, M.; Porzi, G.; Sandri, S. J. Chem. Res. (S) 1993 , 318 , 2125.
9. Energy calculations were performed by the AM1 method (HyperChem Program, 1994) using the ‘Polak-Ribiere algorithm’ (RMS gradient 0.01 kcal).
10. D=44.5 (c 0.95, 1N HCl).