Determination of the absolute configuration and enantiomeric purity of chiral primary alcohols by 1H NMR of 9-anthrylmethoxyacetates

Tetrahedron Asymmetry

Volumn 7, Issue 8, 1996, Pages 2195-2198

  Ferreiro, M J ^b   Latypov, Sh K ^a,b   Quinoa E ^b   Riguera, R ^b  

^a A E ARBUZOV INSTITUTE OF ORGANIC AND PHYSICAL CHEMISTRY   (Russian Federation)

^b Santiago de Compostela Spain   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANOL;

ARTICLE; DERIVATIZATION; DRUG PURITY; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; TECHNIQUE;

EID: 0030221013     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00269-8     Document Type: Article

References (12)

1. 1. a) Trost, B. M.; Belletire, J. L.; Godleski, S.; McDougal, P. G.; Balkovec, J. M. J. Org. Chem. 1986, 51, 2370-2374;
2. b) Pehk, T.; Lippmaa, E.; Lopp, M.; Paju, A.; Borrer B. C.; Taylor R. J. K. Tetrahedron : Asymmetry 1993, 4, 1527-1532;
3. c) Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-519;
4. d) Sullivan, G. R.; Dale, J. A.; Mosher, H. S. J. Org. Chem. 1973, 38, 2143-2147.
5. 2. a) Seco, J. M.; Latypov, Sh. K.; Quiñoá, E.; Riguera, R. Tetrahedron Lett. 1994, 35 , 2921-2924;
6. b) Latypov, Sh. K.; Seco, J. M.; Quiñoá, E.; Riguera, R. J. Org. Chem. 1995, 60, 504-515;
7. c) Seco, J. M.; Latypov, Sh. K.; Quiñoá, E.; Riguera, R. Tetrahedron : Asymmetry 1995, 6, 107-110.
8. RS = δR-δS).
9. 4. Haigh, C. W.; Mallion, R. B. Progress in NMR spectroscopy ; Pergamon Press Ltd, 1980; 13, 303-344.
10. 3 containing TMS as internal standard. The esters were prepared by the standard method without racemization and purified by HPLC. All compounds gave satisfactory analysis and spectroscopic data. The absolute stereochemistry was confirmed by CD.
11. 6. This procedure is equivalent to the comparison between the esters of both enantiomers of the parent alcohol and one enantiomer of the auxiliary reagent (9-AMA).
12. 7. MM calculations were carried out using the Insight II program running on a Silicon Graphics Iris Computer and performed with the CVFF force field. For more details, see ref 2b.