The application of 1H nuclear magnetic resonance spectroscopy for the determination of the absolute configuration of chiral carboxylic acids

Tetrahedron

Volumn 52, Issue 29, 1996, Pages 9841-9852

  Tyrrell, Elizabeth ^a   Tsang, Michael W H ^a   Skinner, George A ^a   Fawcett, John ^b  

^a KINGSTON UNIVERSITY   (United Kingdom)

^b UNIVERSITY OF LEICESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 BENZYLPROPIONIC ACID; 2 METHYLBUTYRIC ACID; 3 (2 BENZYL PROPANOYL) 4 BENZYL 2 OXAZOLIDINONE; 3 (PROPANOYL) 4 BENZYL 2 OXAZOLIDINONE; CARBOXYLIC ACID DERIVATIVE; MANDELIC ACID; UNCLASSIFIED DRUG;

ANISOTROPY; ARTICLE; CHIRALITY; CONFORMATION; DIASTEREOISOMER; ENANTIOMER; ESTERIFICATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030586223     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00516-9     Document Type: Article

References (22)

1. 1. Parker, D. Chem. Rev. 1991., 91, 1441.
2. 2. Raban, M.; Mislow, K. Tetrahedron Lett., 1965, 48, 4249. Raban, M.; Mislow, K. Tetrahedron Lett., 1966, 33, 3961.
3. 2. Raban, M.; Mislow, K. Tetrahedron Lett., 1965, 48, 4249. Raban, M.; Mislow, K. Tetrahedron Lett., 1966, 33, 3961.
4. 3. Raban, M.; Mislow, K. Top. Stereochemistry., 1967, 2, 199. Mosher, H.S.; Dale, J.A.; Dull, D.L. J. Org. Chem., 1969, 34, 2543. Mosher, H.S.; Dale, J.A. J. Am. Chem. Soc., 1973, 95, 512.
5. 3. Raban, M.; Mislow, K. Top. Stereochemistry., 1967, 2, 199. Mosher, H.S.; Dale, J.A.; Dull, D.L. J. Org. Chem., 1969, 34, 2543. Mosher, H.S.; Dale, J.A. J. Am. Chem. Soc., 1973, 95, 512.
6. 3. Raban, M.; Mislow, K. Top. Stereochemistry., 1967, 2, 199. Mosher, H.S.; Dale, J.A.; Dull, D.L. J. Org. Chem., 1969, 34, 2543. Mosher, H.S.; Dale, J.A. J. Am. Chem. Soc., 1973, 95, 512.
7. 4. Kakisawa, H.; Kashman, Y.; Kusumi, T.; Ohtani, I. J. Am. Chem. Soc., 1991, 113, 4092. Heumann, A. J.Chem. Soc., Chem. Commun., 1993, 113. McFarlane, A.; Bookham, L.J. J. Chem. Soc., Chem. Commun., 1993, 1352. Trost, B.M.;Bunt, R.C.; Pulley, S.R. J. Org. Chem., 1994, 59, 4202. Riguera, R.; Quinoa, E.; Seco, J.M.; Latypov, S.K. J. Org. Chem., 1995, 60, 1538
8. 4. Kakisawa, H.; Kashman, Y.; Kusumi, T.; Ohtani, I. J. Am. Chem. Soc., 1991, 113, 4092. Heumann, A. J.Chem. Soc., Chem. Commun., 1993, 113. McFarlane, A.; Bookham, L.J. J. Chem. Soc., Chem. Commun., 1993, 1352. Trost, B.M.;Bunt, R.C.; Pulley, S.R. J. Org. Chem., 1994, 59, 4202. Riguera, R.; Quinoa, E.; Seco, J.M.; Latypov, S.K. J. Org. Chem., 1995, 60, 1538
9. 4. Kakisawa, H.; Kashman, Y.; Kusumi, T.; Ohtani, I. J. Am. Chem. Soc., 1991, 113, 4092. Heumann, A. J.Chem. Soc., Chem. Commun., 1993, 113. McFarlane, A.; Bookham, L.J. J. Chem. Soc., Chem. Commun., 1993, 1352. Trost, B.M.;Bunt, R.C.; Pulley, S.R. J. Org. Chem., 1994, 59, 4202. Riguera, R.; Quinoa, E.; Seco, J.M.; Latypov, S.K. J. Org. Chem., 1995, 60, 1538
10. 4. Kakisawa, H.; Kashman, Y.; Kusumi, T.; Ohtani, I. J. Am. Chem. Soc., 1991, 113, 4092. Heumann, A. J.Chem. Soc., Chem. Commun., 1993, 113. McFarlane, A.; Bookham, L.J. J. Chem. Soc., Chem. Commun., 1993, 1352. Trost, B.M.;Bunt, R.C.; Pulley, S.R. J. Org. Chem., 1994, 59, 4202. Riguera, R.; Quinoa, E.; Seco, J.M.; Latypov, S.K. J. Org. Chem., 1995, 60, 1538
11. 4. Kakisawa, H.; Kashman, Y.; Kusumi, T.; Ohtani, I. J. Am. Chem. Soc., 1991, 113, 4092. Heumann, A. J.Chem. Soc., Chem. Commun., 1993, 113. McFarlane, A.; Bookham, L.J. J. Chem. Soc., Chem. Commun., 1993, 1352. Trost, B.M.;Bunt, R.C.; Pulley, S.R. J. Org. Chem., 1994, 59, 4202. Riguera, R.; Quinoa, E.; Seco, J.M.; Latypov, S.K. J. Org. Chem., 1995, 60, 1538
12. 5. Trost, B.M.; Belletire, J.L.; Godleski, S.; McDougal, P.G.; Balkovac, J.M. J. Org. Chem., 1986, 51, 2370.
13. 6. Available from Aldrich Chemical Co. Ltd. Ref: 25, 154-2.
14. 7. Parker, D. J.Chem. Soc. Perkin Trans. II., 1983, 83,
15. 8. As the absolute configuration of the mandelate was known and the chiral acids were either readily available in either enantiomeric form (entries 5,6, & 7 [Table 1], were synthesised in both enantiomeric forms (entries 3,4, 8, 9 10 [table 1] or the (R)-enantiomer only was synthesised (entries 1,2 [table 1]), the signals for the major component must be representative of either the R-S diastereomer or of the S-S diastereomer.
16. 3 (probe temperature of 23° C), analysis of the spectra obtained from 4%, 4.5% and 5% solutions (up to a two and a half fold increase of sample) showed that there was no concentration dependence upon the chemical shift difference..
17. 10 Evans, D.A.; Takacs, J.M. Tetrahedron Letters., 1980, 21, 4233. Evans, D.A.; Takacs, J.M.; McGee, L.R.; Ennis, M.D.; Mathre, D.J.; Bartoli, J. Pure & Appl. Chem., 1981, 53, 1109. Evans, D.A.; Bartoli, J. Tetrahedron Letters, 1982, 23, 807.
18. 10 Evans, D.A.; Takacs, J.M. Tetrahedron Letters., 1980, 21, 4233. Evans, D.A.; Takacs, J.M.; McGee, L.R.; Ennis, M.D.; Mathre, D.J.; Bartoli, J. Pure & Appl. Chem., 1981, 53, 1109. Evans, D.A.; Bartoli, J. Tetrahedron Letters, 1982, 23, 807.
19. 10 Evans, D.A.; Takacs, J.M. Tetrahedron Letters., 1980, 21, 4233. Evans, D.A.; Takacs, J.M.; McGee, L.R.; Ennis, M.D.; Mathre, D.J.; Bartoli, J. Pure & Appl. Chem., 1981, 53, 1109. Evans, D.A.; Bartoli, J. Tetrahedron Letters, 1982, 23, 807.
20. -3 respectively. 1. G.M. Sheldrick, SHELXTL-pc Release 4.2, Siemens Analytical X-ray Instruments, Madison, WI, 1991.
21. 2. G.M. Sheldrick, SHELX-93, Program for Crystal Structure Refinement, University of Gottingen, 1993.
22. 12. Still, W.C.; Kahn, M.; Mitra, A. J. Org. Chem., 1978, 43, 2923.