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Volumn 10, Issue 15, 1999, Pages 2927-2934

A new method for the determination of the absolute stereochemistry of aromatic and heteroaromatic alkanols using Mosher's esters

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; AROMATIC COMPOUND; PHENYLACETIC ACID DERIVATIVE;

EID: 0033618602     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00295-5     Document Type: Article
Times cited : (54)

References (41)
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    • Yamaguchi, S. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: London, 1983; Vol. 1, pp. 125-152; Parker, D. Chem. Rev. 1991, 91, 1441-1457. Numerous other derivatives have been proposed, but still await wide scale acceptance; arylmethoxyacetic esters, Seco, J. M.; Latypov, Sh.; Quinoa, E.; Riguera, R. Tetrahedron: Asymmetry 1995, 6, 107-110; Kusumi, T.; Takahashi, H.; Xu, P.; Fukushima, T.; Asakawa, Y.; Hashimoto, T.; Kan, Y.; Inouye, Y. Tetrahedron Lett. 1994, 35, 4397-4400; β-fucofuranosides, Kobayashi, M. Tetrahedron 1998, 54, 10987-10998; tetra-O-benzoyl-β- glucopyranosides, Trujillo, M.; Morales, E. Q.; Vazquez, J. T. J. Org. Chem. 1994, 59, 6637-6642.
    • (1991) Chem. Rev. , vol.91 , pp. 1441-1457
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    • Yamaguchi, S. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: London, 1983; Vol. 1, pp. 125-152; Parker, D. Chem. Rev. 1991, 91, 1441-1457. Numerous other derivatives have been proposed, but still await wide scale acceptance; arylmethoxyacetic esters, Seco, J. M.; Latypov, Sh.; Quinoa, E.; Riguera, R. Tetrahedron: Asymmetry 1995, 6, 107-110; Kusumi, T.; Takahashi, H.; Xu, P.; Fukushima, T.; Asakawa, Y.; Hashimoto, T.; Kan, Y.; Inouye, Y. Tetrahedron Lett. 1994, 35, 4397-4400; β-fucofuranosides, Kobayashi, M. Tetrahedron 1998, 54, 10987-10998; tetra-O-benzoyl-β- glucopyranosides, Trujillo, M.; Morales, E. Q.; Vazquez, J. T. J. Org. Chem. 1994, 59, 6637-6642.
    • (1995) Tetrahedron: Asymmetry , vol.6 , pp. 107-110
    • Seco, J.M.1    Latypov, Sh.2    Quinoa, E.3    Riguera, R.4
  • 4
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    • Yamaguchi, S. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: London, 1983; Vol. 1, pp. 125-152; Parker, D. Chem. Rev. 1991, 91, 1441-1457. Numerous other derivatives have been proposed, but still await wide scale acceptance; arylmethoxyacetic esters, Seco, J. M.; Latypov, Sh.; Quinoa, E.; Riguera, R. Tetrahedron: Asymmetry 1995, 6, 107-110; Kusumi, T.; Takahashi, H.; Xu, P.; Fukushima, T.; Asakawa, Y.; Hashimoto, T.; Kan, Y.; Inouye, Y. Tetrahedron Lett. 1994, 35, 4397-4400; β-fucofuranosides, Kobayashi, M. Tetrahedron 1998, 54, 10987-10998; tetra-O-benzoyl-β- glucopyranosides, Trujillo, M.; Morales, E. Q.; Vazquez, J. T. J. Org. Chem. 1994, 59, 6637-6642.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 4397-4400
    • Kusumi, T.1    Takahashi, H.2    Xu, P.3    Fukushima, T.4    Asakawa, Y.5    Hashimoto, T.6    Kan, Y.7    Inouye, Y.8
  • 5
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    • Yamaguchi, S. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: London, 1983; Vol. 1, pp. 125-152; Parker, D. Chem. Rev. 1991, 91, 1441-1457. Numerous other derivatives have been proposed, but still await wide scale acceptance; arylmethoxyacetic esters, Seco, J. M.; Latypov, Sh.; Quinoa, E.; Riguera, R. Tetrahedron: Asymmetry 1995, 6, 107-110; Kusumi, T.; Takahashi, H.; Xu, P.; Fukushima, T.; Asakawa, Y.; Hashimoto, T.; Kan, Y.; Inouye, Y. Tetrahedron Lett. 1994, 35, 4397-4400; β-fucofuranosides, Kobayashi, M. Tetrahedron 1998, 54, 10987-10998; tetra-O-benzoyl-β- glucopyranosides, Trujillo, M.; Morales, E. Q.; Vazquez, J. T. J. Org. Chem. 1994, 59, 6637-6642.
    • (1998) Tetrahedron , vol.54 , pp. 10987-10998
    • Kobayashi, M.1
  • 6
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    • Yamaguchi, S. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: London, 1983; Vol. 1, pp. 125-152; Parker, D. Chem. Rev. 1991, 91, 1441-1457. Numerous other derivatives have been proposed, but still await wide scale acceptance; arylmethoxyacetic esters, Seco, J. M.; Latypov, Sh.; Quinoa, E.; Riguera, R. Tetrahedron: Asymmetry 1995, 6, 107-110; Kusumi, T.; Takahashi, H.; Xu, P.; Fukushima, T.; Asakawa, Y.; Hashimoto, T.; Kan, Y.; Inouye, Y. Tetrahedron Lett. 1994, 35, 4397-4400; β-fucofuranosides, Kobayashi, M. Tetrahedron 1998, 54, 10987-10998; tetra-O-benzoyl-β-glucopyranosides, Trujillo, M.; Morales, E. Q.; Vazquez, J. T. J. Org. Chem. 1994, 59, 6637-6642.
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  • 7
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    • Sullivan, G. R.; Dale, J. A.; Mosher, H. S. J. Org. Chem. 1973, 38, 2143-2147 for criticism of this method see: Ohtani, I.; Kusumi, T.; Ishitsuka, M. O.; Kakisawa, H. Tetrahedron Lett. 1989, 30, 3147-3150; Ref. 4.
    • (1973) J. Org. Chem. , vol.38 , pp. 2143-2147
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  • 8
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    • Ref. 4
    • Sullivan, G. R.; Dale, J. A.; Mosher, H. S. J. Org. Chem. 1973, 38, 2143-2147 for criticism of this method see: Ohtani, I.; Kusumi, T.; Ishitsuka, M. O.; Kakisawa, H. Tetrahedron Lett. 1989, 30, 3147-3150; Ref. 4.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 3147-3150
    • Ohtani, I.1    Kusumi, T.2    Ishitsuka, M.O.3    Kakisawa, H.4
  • 20
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    • Yamaguchi, S.; Kabuto, K. Bull. Chem. Soc. Jpn. 1977, 50, 3033-3038; Furukawa, J.; Iwasaki, S.; Okuda, S. Tetrahedron Lett. 1983, 24, 5257-5260.
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    • It is not widely appreciated that conversion of MTPA to the corresponding acid chloride results in a change in the Cahn-Ingold-Prelog assignment of absolute stereochemistry, which is restored to the original assignment in the ester. In cases of ambiguity, the data has either been discarded, the assignment has been based on the quoted rotation [(S)-(-)-MTPA→(R)-(-)-MTPA-Cl→(S)-MTPA-OR] or the original author has been contacted. Joshi, J. B.; Pelletier, S. W. Heterocycles 1999, 51, 183-184.
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    • note
    • Unfortunately, papers reporting application of the 'modified Mosher method', almost invariably do not report the chemical shift of the methoxy group.
  • 28
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    • 3) δ (R,S) 6.08, 3.45; (R,R) 6.13, 3.47, which is contradictory to the previous entries. It appears that the δ 3.45 shift is a typographical error and should be δ 3.54. Streinz, L.; Svatos, A.; Vrkoc, J.; Meinwald, J. J. Chem. Soc., Perkin Trans. 1 1994, 3509-3512.
    • (1994) J. Chem. Soc., Perkin Trans. 1 , pp. 3509-3512
    • Streinz, L.1    Svatos, A.2    Vrkoc, J.3    Meinwald, J.4
  • 31
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    • Collins, S.; Kuntz, B. A.; Hong, Y. J. Org. Chem. 1989, 54, 4154-4158. We thank Prof. Collins for providing additional information regarding this paper.
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  • 38


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