The use of ethyl 2-(9-anthryl)-2-hydroxyacetate for assignment of the absolute configuration of carboxylic acids by1H NMR

Tetrahedron Asymmetry

Volumn 8, Issue 7, 1997, Pages 1015-1018

  Ferreiro, María J ^a   Latypov, Shamil K ^a,b   Quiñoá, Emilio ^a   Riguera, Ricardo ^a  

^a Santiago de Compostela Spain   (Spain)

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

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID;

ARTICLE; CHIRALITY; DERIVATIZATION; DRUG STRUCTURE; MODEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; THEORY;

EID: 0030985551     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00081-5     Document Type: Article

References (14)

1. Ferreiro, M. J.; Latypov, Sh. K.; Quiñoá, E.; Riguera, R. Tetrahedron: Asymmetry 1996, 7, 2195-2198.
2. a) Nagai, Y.; Kusumi, T. Tetrahedron Lett. 1995, 36, 1853-1856.
3. b) Tyrrell, E.; Tsang, M. W. H.; Skinner, G. A.; Fawcett, J. Tetrahedron 1996, 52, 9841-9852.
4. c) Fukushi, Y.; Shigematsu, K; Mizutani, J.; Tahara, S. Tetrahedron Lett 1996, 37, 4737-4740.
5. a) Latypov, Sh.K.; Seco, J. M.; Quiñoá, E.; Riguera, R. J. Org. Chem. 1995, 60, 504-515.
6. b) Latypov, Sh.K.; Seco, J. M; Quiñoá, E.; Riguera, R. J. Org. Chem. 1995, 60, 1538-1435.
7. MM, semiempirical and aromatic shielding effect calculations, were carried out as indicated in Ref. 3a.
8. 1 refers to the carbon e aring the hydroxyl group in the alcohol moiety, although it is carbon 2 in the systematic name.
9. Comparison of the aromatic shielding calculated for each conformer with the experimental value reveals an energy difference between conformers in good agreement with the AMI calculated one.
10. RS=δ(R)-δ(S)].
11. D=+83.5. For spectroscopic data of 5 (NMR, MS, UV, IR, CD), see Ref.3a.
12. 2)].
13. 3 containing TMS as internal standard. The esters were prepared by the standard method (see Ref. 3a) without racemization and purified by HPLC. All compounds gave satisfactory elemental analysis and spectroscopic data.
14. RS values of the esters of acids 6 and 10 with alcohol 3, see Ref. 2b.