Resolution and determination of the enantiomeric purity and absolute configurations of α-aryl-α-hydroxymethanephosphonates

Tetrahedron Asymmetry

Volumn 7, Issue 8, 1996, Pages 2173-2176

  Pirkle, William H ^a   Brice, L Jonathan ^a   Widlanski, Theodore S ^b   Roestamadji, Juliatiek ^b  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^b INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CHIRALITY; DRUG PURIFICATION; DRUG PURITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; TECHNIQUE;

EID: 0030221427     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00263-7     Document Type: Article

References (6)

1. 1. Wynberg, H.; Smaardijk A. A. Tet. Lett. 1983, 24, 5899.
2. 2. Smaardijk, A. A.; Noorda, S.; van Bolhuis F.; Wynberg H. Tet. Lett. 1985, 26, 493.
3. 3. Yokomatsu, T.; Yamagishi, T.; Shibuya S. Tet. Asymm. 1993, 1779 and references therein.
4. 4. Pirkle W.; Welch C. J. Chromatography, 1994 683, 347 and references therein.
5. 5. Additional discussion of the mechanism(s) by which CSP 1 differentiates between enantiomers is to be found in: Pirkle, W.; Koscho, M.; and Wu, Z. J. Chromatography 1996, 726, 91.
6. 6. The column used in these studies is a Regis Technologies 4.6 x 250 mm (S,S )-Whelk-O 1. The absolute configuration of the selector used in the (S,S)-Whelk-O 1 is incorrectly designated and should properly be (3R, 4S). It is the configuration at C-4 which determines elution order. Hence, the incorrect designation should not lead to confusion concerning expected elution order. The (S,S) assignment was originally made for the CSP bearing an eleven-carbon tethering moiety. The use of a three-carbon tether improves performance but causes a priority inversion at C-3, necessitating a change in the stereochemical descriptor.