Application of phenylglycine methyl ester (PGME) to determination of the absolute configuration of carboxylic acids having phenylalkyl group

Chirality

Volumn 9, Issue 5-6, 1997, Pages 550-555

  Yabuuchi, Tetsuya ^a   Ooi, Takashi ^a   Kusumi, Takenori ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

Absolute configuration; Chiral anisotropic reagent; Long chain carboxylic acid; Mosher's method; NMR

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; GLYCINE METHYL ESTER; PHENYLGLYCINE; REAGENT;

ANISOTROPY; ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; MOLECULAR INTERACTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOISOMERISM;

EID: 0030954724     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1997)9:5/6<550::AID-CHIR23>3.0.CO;2-M     Document Type: Article

References (16)

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6. (b) Latypov, Sh.K., Seco, J.M., Quiñoà, E., Riguera, R. Conformational structure and dynamics of arylmethoxyacetates: DNMR spectroscopy and aromatic shielding effect. J. Org. Chem. 60:504-515, 1995.
7. (c) Fukushi, Y., Yajima, C., Mizutani, J. Prelacinan-7-ol, a novel sesquiterpene from Rudbeckia laciniata. Tetrahedron Lett. 35:599-602, 1994.
8. Kusumi, T., Takahashi, H., Ping X., Fukushima, T., Asakawa, Y., Hashimoto, T., Kan, Y. New chiral anisotropic reagents, NMR tools to elucidate the absolute configurations of long-chain organic compounds. Tetrahedron Lett 35:4397-4400, 1994.
9. Nagai, Y., Kusumi, T. New chiral anisotropic reagents for determining the absolute configuration of carboxylic acids. Tetrahedron Lett. 36: 1853-1856, 1995.
10. Model A is for the secondary alcohols in the modified Mosher's method (see reference 1b.).
11. Unpublished results.
12. Compound A was prepared from the carboxylic acid kindly donated by Professor M. Nishizawa. See, (a) S Nishizawa, M., Minagawa, R., Garcia, D.M., Hatakeyama, S., Yamada, H. Synthesis and characterization of four diastereomers of trehalose-6,6′-dicorynomycolates (TD BH-32). Tetrahedron Lett. 35:5891-5894, 1994.
13. (b) Nishizawa, M., Garcia, D.M., Minagawa, R., Noguchi, Y., Imagawa, H., Yamada, H. Efficient synthesis of four trehalose dicorynomycolates (TDCMs) and their immuno-adjuvant activities. Synlett. 5:452-454, 1996.
14. Davies, S.G., Doisneau, G.M., Prodger, J.C., Sanganee, H.J. Asymmetric aldol and alkylation reactions mediated by the "quat" chiral auxiliary (R)-(-)-5-methyl-3,3-dimethyl-2-pyrrolidinone. Tetrahedron Lett. 35:2373-2376, 1994.
15. Anastasis, P., Freer, I., Pverton, K.H., Picken, D., Rycroft, D.S., Singh, S.B. On the role of leucine in terpenoid metabolism. J. Chem. Soc. Perkin I Trans. 2427-2433, 1987.
16. S-S (2). In the present case, because (S)-PGME was used for the racemic acid, R-S and S-S amides were obtained. The Δδ values shown in Tables 1 and 2 as well as in Scheme 4 are those calculated by equation (2). The positive and negative signs are, therefore, significant only for the (R)-carboxylic acids.