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Volumn 54, Issue 6, 1989, Pages 1295-1304

Arenesulfonate Derivatives of Homochiral Glycidol: Versatile Chiral Building Blocks for Organic Synthesis

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EID: 0000209289     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00267a014     Document Type: Article
Times cited : (203)

References (58)
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    • Isolation of the alcohol 4 resulting from pathway c circumvents the potential problem of loss of optical purity due to poor regioselectivity. Advantage has been taken of this fact in more than one synthesis involving optically active epichlorohydrin
    • Isolation of the alcohol 4 resulting from pathway c circumvents the potential problem of loss of optical purity due to poor regioselectivity. Advantage has been taken of this fact in more than one synthesis involving optically active epichlorohydrin. (a) Yo, E.; Nakagawa, K.; Hoshino, Y. Chem. Pharm. Bull. 1981, 29, 2157.
    • (1981) Chem. Pharm. Bull. , vol.29 , pp. 2157
    • Yo, E.1    Nakagawa, K.2    Hoshino, Y.3
  • 9
    • 0003491250 scopus 로고
    • The pronounced steric hindrance of 2,4,6-triisopropylbenzene-sulfonyl chloride has been exploited in a variety of applications, particularly in carbohydrate and nucleoside chemistry. See: Eds.; Pergamon: Oxford, Vol. 5 and references cited therein.
    • The pronounced steric hindrance of 2,4,6-triisopropylbenzene-sulfonyl chloride has been exploited in a variety of applications, particularly in carbohydrate and nucleoside chemistry. See: Comprehensive Organic Chemistry; Barton, D., Ollis, W.,D., Eds.; Pergamon: Oxford, 1979; Vol. 5 and references cited therein.
    • (1979) Comprehensive Organic Chemistry
    • Ollis, W.1    Barton, D.2
  • 11
    • 85022313799 scopus 로고    scopus 로고
    • Mechanism and Theory in Organic Chemistry, 2nd ed.; Harper & Row: New York, 1981: pp 339–342
    • Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 2nd ed.; Harper & Row: New York, 1981: pp 339–342.
    • Lowry, T.H.1    Richardson, K.S.2
  • 16
    • 0023915750 scopus 로고
    • For syntheses of γ-amino-β-hydroxybutyric acid (GABOB) and carnitine, see: Takano, S.; Yanase, M.; Sekiguchi, Y.; Ogasawara, K. Tetrahedron Lett. 1987, 28, 1783. Renaud, P.; Seebach, D. Synthesis 1986, 424. Rajashekhar, B.; Kaiser, E. T. J. Org. Chem. 1985, 50, 5480. Pellegata, R.; Dosi, I.; Villa, M.; Lesma, G.; Palmisano, G. Tetrahedron 1985, 41, 5607. Rossiter, B. E.; Sharpless, K. B. J. Org, Chem. 1984, 49, 3707. Zhou, B.; Gopalan, A. S.; VanMiddlesworth, F.; Shieh, W. R.; Sih, C. J. J. Am, Chem. Soc. 1983, 105, 5925.
    • For syntheses of γ-amino-β-hydroxybutyric acid (GABOB) and carnitine, see: Bianchi, D.; Cabri, W.; Cesti, P.; Francalanci, F.; Ricci, M. J. Org. Chem. 1988, 53, 104. Takano, S.; Yanase, M.; Sekiguchi, Y.; Ogasawara, K. Tetrahedron Lett. 1987, 28, 1783. Renaud, P.; Seebach, D. Synthesis 1986, 424. Rajashekhar, B.; Kaiser, E. T. J. Org. Chem. 1985, 50, 5480. Pellegata, R.; Dosi, I.; Villa, M.; Lesma, G.; Palmisano, G. Tetrahedron 1985, 41, 5607. Rossiter, B. E.; Sharpless, K. B. J. Org, Chem. 1984, 49, 3707. Zhou, B.; Gopalan, A. S.; VanMiddlesworth, F.; Shieh, W. R.; Sih, C. J. J. Am, Chem. Soc. 1983, 105, 5925.
    • (1988) J. Org. Chem. , vol.53 , pp. 104
    • Bianchi, D.1    Cabri, W.2    Cesti, P.3    Francalanci, F.4    Ricci, M.5
  • 18
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    • The preparation of oxazolines from epoxides by treatment with a nitrile and BF3.OEt2has been reported previously
    • The preparation of oxazolines from epoxides by treatment with a nitrile and BF3.OEt2has been reported previously: Lindsay Smith, J. R.; Norman, R. O. C.; Stillings, M. R. J. Chem. Soc., Perkin Trans. 1 1975, 1200.
    • (1975) J. Chem. Soc., Perkin Trans. , pp. 1200
    • Smith, J.R.1    Norman, R.O.C.2    Stillings, M.R.3
  • 20
    • 0001641492 scopus 로고    scopus 로고
    • Tetrahedron Lett. 1983,24, 391
    • Yamaguchi, M.; Hirao, I. Tetrahedron Lett. 1983,24, 391.
    • Yamaguchi, M.1    Hirao, I.2
  • 51
    • 0002714675 scopus 로고
    • Melting points are uncorrected. Flash chromatography was performed on Merck silica gel 60 (230–400 mesh) as described by Still All commercial reagents were used as received unless otherwise noted. (±)-Glycidol (Aldrich) was distilled under reduced pressure and stored at -20 °C. (2R)-and (2S)-glycidol were prepared as previously described.2 Copper(I) iodide (99.999%) was used as received from Cerac.
    • Melting points are uncorrected. Flash chromatography was performed on Merck silica gel 60 (230–400 mesh) as described by Still [Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923]. All commercial reagents were used as received unless otherwise noted. (±)-Glycidol (Aldrich) was distilled under reduced pressure and stored at -20 °C. (2R)-and (2S)-glycidol were prepared as previously described.2 Copper(I) iodide (99.999%) was used as received from Cerac.
    • (1978) J. Org. Chem. , vol.43 , pp. 2923
    • Still, W.C.1    Kahn, M.2    Mitra, A.3
  • 54
    • 85022267177 scopus 로고
    • Racemic 2a has been reported previously:
    • Racemic 2a has been reported previously: (a) Pierre, J. L.; Arnaud, P. Bull. Soc. Chim. Fr. 1969, 2868.
    • (1969) Bull. Soc. Chim. Fr. , pp. 2868
  • 55
    • 85007975033 scopus 로고    scopus 로고
    • Yuki Gosei Kagaku Kyokaishi 1964, 22, 553. See also ref 4a
    • Ichikawa, K. Yuki Gosei Kagaku Kyokaishi 1964, 22, 553. See also ref 4a.
    • Ichikawa, K.1
  • 56
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    • This compound has been reported as the racemate: Whalen, D. L. Tetrahedron Lett. 1978, 4973.
    • (1978) Tetrahedron Lett. , pp. 4973
    • Whalen, D.L.1


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