An NMR method for determination of configuration of β-substituted carboxylic acids

Tetrahedron Letters

Volumn 41, Issue 14, 2000, Pages 2289-2293

  Hoye, Thomas R ^a   Hamad, Abdel Sattar S ^a,b   Koltun, Dmitry O ^a   Tennakoon, Manomi A ^a  

^a University of Minnesota   (United States)

^b Ain Shams University   (Egypt)

Author keywords

Carboxylic acids; Configuration; NMR spectroscopy; Stereochemistry

Indexed keywords

BENZYLAMINE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE;

ARTICLE; CHIRALITY; CONFORMATION; DERIVATIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY;

EID: 0034175635     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00163-5     Document Type: Article

References (21)

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7. For example, see: (a) Pirkle, W. H.; Simmons, K. A. J. Org. Chem. 1983, 48, 2520. (b) Pirkle, W. H.; Robertson, M. R.; Hyun, M. H. J. Org. Chem. 1984, 49, 2433.
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9. Hoye, T. R.; Koltun, D. O. J. Am. Chem. Soc. 1998, 120, 4638.
10. 2 are both carbon substituents. A nearly equal number are known in which one of the two is a hetereoatom substituent.
11. (a) Nuzzo, R. G.; Haynie, S. L.; Wilson, M. E.; Whitesides, G. M. J. Org. Chem. 1981 46, 2861.
12. 2, arising from amine attack at the α-branched carbonyl group.
13. In the case of tricarballylic acid anhydride, products arising from α- and β-openings were separated using MPLC.
14. Iwasawa, Y.; Shibata, J.; Nonoshita, K.; Arai, S.; Masaki, H.; Tomimoto, K. Tetrahedron 1996, 52, 13 881.
15. We have found additional examples of analogous amide derivatives of 3-substituted carboxylic acids (i-vi) that complement the NMR data reported in Table 1. The Δδ [=δ (syn)-δ (anti)] value for the relevant protons of the two diastereomers is indicated (with sign) directly beside the relevant proton. (a) Sita, L. R. J. Org. Chem. 1993, 58, 5285.
16. (b) Huffman, J. W.; Lainton, J. A. H.; Banner, W. K.; Duncan, S. G.; Jordan, R. D.; Yu, S.; Dai, D.; Martin, B. R.; Wiley, J. L.; Compton, D. R. Tetrahedron 1997, 53, 1557.
17. (c) Yamamoto, Y.; Iwasa, M.; Sawada, S.; Oda, J. Agric. Biol. Chem. 1990, 54, 3269.
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19. (e) Chapleo, C. B.; Hallett, P.; Lythgoe, B.; Waterhouse, I.; Wright, P. W. J. Chem Soc., Perkin 1 1977, 1211.
20. 11
21. 1H NMR data in Ref. 10f are reversed for syn-vi and anti-vi (although the mp and specific rotation values as reported are associated with the correct diastereomeric structures). The signs and magnitudes of the Δδ values shown in structure vi above are from our NMR data and are unambiguously consistent with the method.