Infelicitous stereochemical nomenclature

Chirality

Volumn 9, Issue 5-6, 1997, Pages 428-430

  Eliel, Ernest L ^a  

^a University of North Carolina at Chapel Hill   (United States)

Author keywords

Chiral; Chirality asymmetric synthesis; Geometrical isomers; Homochiral; Optical isomers; Optical purity; Stereogenic center; Thalidomide

Indexed keywords

THALIDOMIDE;

ARTICLE; CHIRAL CHROMATOGRAPHY; CHIRALITY; ENANTIOMER; ISOMER; NOMENCLATURE; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030929554     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1997)9:5/6<428::AID-CHIR5>3.0.CO;2-1     Document Type: Article

References (11)

1. See also Helmchen, G. Glossary of problematic terms in organic stereochemistry. Enantiomer 1:1996; 4 unnumbered pages following p. 84.
2. Eliel, E.L., Wilen, S.H. Stereochemistry of Organic Compounds. New York: Wiley-Interscience, 1994:1191-1210.
3. See also Gawley, R.E., Aubé, J. Principles of Asymmetric Synthesis. Oxford: Pergamon, 1996:15-40.
4. Brewster, J.H. Racemic, scalemic, holemic. Chem. Eng. News 70:1992, May 18, 3;
5. see also Heathcock, C.H. Alternative to homochiral. Chem. Eng. News 69:1991, February 4, 3.
6. Mislow, K. A commentary on the topological chirality and achirality of molecules. Croat. Chem. Acta 69:485-511, 1996.
7. Cornforth, R.H., Cornforth J.W. How to be right and wrong. Croat. Chem. Acta 69:427-433, 1996.
8. McCasland, G.E. A New General System for the Naming of Stereoisomers. Columbus, OH: Chemical Abstracts Service 1950:2-3.
9. Mislow, K., Siegel, J. Stereoisomerism and local chirality. J. Am. Chem. Soc., 106:3319-3328, 1984.
10. Blaschke, G., Kraft, H.P., Fickentscher, K., Köhler, F. Chromatographische Racemattrennung von Thalidomid und teratogene Wirkung der Enantiomere. Arzneim. Forsch. Drug Res. 29:1640-1642, 1979.
11. Knoche, B., Blaschke, G. Investigations on the in vitro racemization of thalidomide by high-performance liquid chromatography. J. Chromatogr. A 666:235-240, 1994. The half-life for racemization at 37°C in a phosphate buffer (pH 7.4), about 4.5 hr, is reduced to about 10 min in the presence of human serum albumin.