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Volumn 58, Issue 44, 2002, Pages 8985-8991

Enantioselective synthesis of α-hydroxy γ-butyrolactones from an ephedrine-derived morpholine-dione

Author keywords

Allylation; Asymmetric synthesis; Diastereoselectivity; Lactones; Wittig reaction

Indexed keywords

ALPHA HYDROXY GAMMA BUTYROLACTONE; ALPHA HYDROXY GAMMA,GAMMA DIMETHYL GAMMA BUTYROLACTONE; EPHEDRINE; GAMMA BUTYROLACTONE DERIVATIVE; MORPHOLINE DERIVATIVE; MORPHOLINE DIONE; UNCLASSIFIED DRUG;

EID: 0037191097     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01151-1     Document Type: Article
Times cited : (16)

References (13)
  • 1
    • 0034694683 scopus 로고    scopus 로고
    • (a) Gathergood N., Zhuang W., Jorgensen K.A. J. Am. Chem. Soc. 122:2000;12517 (b) Huerta F.F., Santosh Lakshmi Y.R., Baeckvall J.-E. Org. Lett. 2:2000;1037 (c) Quian C., Wang L. Tetrahedron: Asymmetry. 11:2000;2347 (d) Chen C.-J., Chu Y.-Y., Liao Y.-Y., Tsai Z.-H., Wang C.-C., Chen K. Tetrahedron Lett. 40:1999;1141.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 12517
    • Gathergood, N.1    Zhuang, W.2    Jorgensen, K.A.3
  • 4
    • 0011214278 scopus 로고
    • Synthetic applications of 1 were not described
    • . Dione 1 has been prepared earlier as a proof for the reactivity of an activated oxalic acid derivative, see: Rudchenko V.F., Shtamburg V.G., Pleshkova A.P., Kostyanovskii R.G. Bull. Acad. Sci. USSR Div. Chem. Sci. (Engl. Transl.). 30:1981;825. For a preparation of racemic 1 see: Drefahl G., Hartmann M., Skurk A. Chem. Ber. 96:1963;1011. Synthetic applications of 1 were not described.
    • (1981) Bull. Acad. Sci. USSR Div. Chem. Sci. (Engl. Transl.) , vol.30 , pp. 825
    • Rudchenko, V.F.1    Shtamburg, V.G.2    Pleshkova, A.P.3    Kostyanovskii, R.G.4
  • 5
    • 0000943833 scopus 로고
    • . The stereochemical assignment is based on the reported trend in chemical shift for the olefinic methine protons in (E) and (Z) benzylidenecamphor derivatives, see: Kossanyi J., Furth B., Morizur J.P. Tetrahedron. 26:1970;395.
    • (1970) Tetrahedron , vol.26 , pp. 395
    • Kossanyi, J.1    Furth, B.2    Morizur, J.P.3
  • 6
    • 0000862469 scopus 로고    scopus 로고
    • . The stereochemistry at the hemiacetal centre has been confirmed in an earlier study by X-ray crystallography, see: Pansare S.V., Ravi R.G., Jain R.P. J. Org. Chem. 63:1998;4120.
    • (1998) J. Org. Chem. , vol.63 , pp. 4120
    • Pansare, S.V.1    Ravi, R.G.2    Jain, R.P.3
  • 7
    • 0028111703 scopus 로고
    • . For the application of other aminoalcohol based morpholinones in the asymmetric synthesis of amino acids, see: (a) Cox G.G., Harwood L.M. Tetrahedron: Asymmetry. 9:1994;1669 (b) Sinclair P.J., Zhai D., Reibenspies J., Williams R.M. J. Am. Chem. Soc. 108:1986;1103.
    • (1994) Tetrahedron: Asymmetry , vol.9 , pp. 1669
    • Cox, G.G.1    Harwood, L.M.2
  • 12
    • 0011234811 scopus 로고    scopus 로고
    • note
    • (b) The enantiomeric excess of the lactones was determined by GC analysis with a HP Chiral (20% permethylated β-cyclodextrin) column (30 m×0.32 mm×0.25 μm).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.